Welcome to LookChem.com Sign In|Join Free

CAS

  • or
Reserpine is a complex alkaloid with significant pharmaceutical importance, known for its role as an antihypertensive and antipsychotic agent. It features a hydroisoquinoline core structure, which can be synthesized through various methods, including intramolecular Diels-Alder reactions using vinyl imidates or amino-Claisen rearrangements of zwitterionic N-vinylisoquinuclidenes. These synthetic approaches highlight its stereochemical complexity and the potential for efficient construction of its pentacyclic skeleton, making it a valuable target for medicinal chemistry and drug development.

50-55-5 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 50-55-5 Structure
  • Basic information

    1. Product Name: Reserpine
    2. Synonyms: RESERPINE;3,4,5-TRIMETHOXYBENZOYL METHYL RESERPATE;11,17-DIMETHOXY-18-[(3,4,5-TRIMETHOXYBENZOYL)OXY]YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER;METHYL RESERPATE;METHYL RESERPATE 3,4,5-TRIMETHOXYBENZOIC ACID ESTER;l -Carpserp;(3beta,16beta,17alpha,18beta,20alpha)-methyleste;,methylester,(3beta,16beta,17alpha,18beta,20alpha)-
    3. CAS NO:50-55-5
    4. Molecular Formula: C33H40N2O9
    5. Molecular Weight: 608.68
    6. EINECS: 200-047-9
    7. Product Categories: Miscellaneous Natural Products;Alkaloids;Biochemistry;Indole Alkaloids;Dopaminergics;Neurotransmitters;Others;Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;SERPASIL;Inhibitors
    8. Mol File: 50-55-5.mol
  • Chemical Properties

    1. Melting Point: ~265 °C (dec.)
    2. Boiling Point: 655.12°C (rough estimate)
    3. Flash Point: 22℃
    4. Appearance: off-white crystalline powder
    5. Density: 1.2336 (rough estimate)
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 177 ° (C=1, DMF)
    8. Storage Temp.: 2-8°C
    9. Solubility: Practically insoluble in water, very slightly soluble in ethanol (96 per cent).
    10. PKA: 6.6(at 25℃)
    11. Water Solubility: Soluble in water.
    12. Stability: Stable, but darkens slowly in light. Combustible. Incompatible with strong acids, reducing agents, oxidizing agents.
    13. Merck: 14,8145
    14. BRN: 102014
    15. CAS DataBase Reference: Reserpine(CAS DataBase Reference)
    16. NIST Chemistry Reference: Reserpine(50-55-5)
    17. EPA Substance Registry System: Reserpine(50-55-5)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 22-67-36-10
    3. Safety Statements: 22-36/37/39-26
    4. RIDADR: 3077
    5. WGK Germany: 3
    6. RTECS: ZG0350000
    7. F: 10-23
    8. TSCA: Yes
    9. HazardClass: N/A
    10. PackingGroup: II
    11. Hazardous Substances Data: 50-55-5(Hazardous Substances Data)

50-55-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 50-55-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 50-55:
(4*5)+(3*0)+(2*5)+(1*5)=35
35 % 10 = 5
So 50-55-5 is a valid CAS Registry Number.
InChI:InChI=1/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/p+1/t18-,22+,24-,27+,28+,31+/m1/s1

50-55-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (R0007)  Reserpine  >98.0%(HPLC)(T)

  • 50-55-5

  • 1g

  • 650.00CNY

  • Detail
  • TCI America

  • (R0007)  Reserpine  >98.0%(HPLC)(T)

  • 50-55-5

  • 5g

  • 1,870.00CNY

  • Detail
  • Alfa Aesar

  • (L03506)  Reserpine, 99%   

  • 50-55-5

  • 1g

  • 614.0CNY

  • Detail
  • Alfa Aesar

  • (L03506)  Reserpine, 99%   

  • 50-55-5

  • 5g

  • 2364.0CNY

  • Detail
  • Sigma-Aldrich

  • (83580)  Reserpine  crystallized, ≥99.0% (HPLC)

  • 50-55-5

  • 83580-1G

  • 174.33CNY

  • Detail
  • Sigma-Aldrich

  • (83580)  Reserpine  crystallized, ≥99.0% (HPLC)

  • 50-55-5

  • 83580-5G

  • 592.02CNY

  • Detail
  • USP

  • (1601000)  Reserpine  United States Pharmacopeia (USP) Reference Standard

  • 50-55-5

  • 1601000-200MG

  • 4,662.45CNY

  • Detail

50-55-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name reserpine

1.2 Other means of identification

Product number -
Other names methyl reserpate 3,4,5-trimethoxybenzoic acid ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fuels and fuel additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-55-5 SDS

50-55-5Synthetic route

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; nitrate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; nitrate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With acetic acid; zinc
ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; perchlorate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; perchlorate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With perchloric acid; zinc
Isoreserpin
482-85-9

Isoreserpin

A

reserpine
50-55-5

reserpine

B

C33H42N2O9
16625-52-8

C33H42N2O9

C

2,3-secoreserpine
16625-53-9

2,3-secoreserpine

Conditions
ConditionsYield
With acetic acid; zinc for 12h; Heating;A 195 mg
B 70 mg
C 22 mg
3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

methyl reserpate
2901-66-8

methyl reserpate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane Ambient temperature; Yield given;
With pyridine at 20℃; for 96h;
(+-)-reserpine

(+-)-reserpine

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With camphor-10-sulfonic acid
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-44-2

(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
2: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
3: Ag2O; CaSO4 / 20 h
4: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
5: MgSO4 / acetonitrile / 1 h
6: aq. HCl / tetrahydrofuran / 30 h / 20 °C
7: pyridine / 96 h / 20 °C
View Scheme
(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester
871938-46-4

(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
2: MgSO4 / acetonitrile / 1 h
3: aq. HCl / tetrahydrofuran / 30 h / 20 °C
4: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: MgSO4 / acetonitrile / 1 h
2: aq. HCl / tetrahydrofuran / 30 h / 20 °C
3: pyridine / 96 h / 20 °C
View Scheme
(1R,5S,6S,7R,9S)-7-Hydroxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

(1R,5S,6S,7R,9S)-7-Hydroxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Ag2O; CaSO4 / 20 h
2: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
3: MgSO4 / acetonitrile / 1 h
4: aq. HCl / tetrahydrofuran / 30 h / 20 °C
5: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
2: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
3: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
4: Ag2O; CaSO4 / 20 h
5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
6: MgSO4 / acetonitrile / 1 h
7: aq. HCl / tetrahydrofuran / 30 h / 20 °C
8: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(furan-2-yl-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-43-1

(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(furan-2-yl-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
2: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
3: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
4: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
5: Ag2O; CaSO4 / 20 h
6: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
7: MgSO4 / acetonitrile / 1 h
8: aq. HCl / tetrahydrofuran / 30 h / 20 °C
9: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-5-oxo-7-(toluene-4-sulfonyloxymethyl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-45-3

(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-5-oxo-7-(toluene-4-sulfonyloxymethyl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
2: Ag2O; CaSO4 / 20 h
3: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
4: MgSO4 / acetonitrile / 1 h
5: aq. HCl / tetrahydrofuran / 30 h / 20 °C
6: pyridine / 96 h / 20 °C
View Scheme
(3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

(3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / tetrahydrofuran / 30 h / 20 °C
2: pyridine / 96 h / 20 °C
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-7-methoxy-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester
185810-96-2

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-7-methoxy-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: pivalic acid / benzene / Heating
2: pivalic acid / toluene / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: 56 mg / pivalic acid / toluene / 0.83 h / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester
185810-94-0

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: pivalic acid / benzene / Heating
3: pivalic acid / toluene / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 9 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: 56 mg / pivalic acid / toluene / 0.83 h / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid 4-methyl ester
1055030-50-6

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid 4-methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: pivalic acid / benzene / Heating
4: pivalic acid / toluene / Heating
5: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
6: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
7: aq. HF / acetonitrile / 0.5 h / Ambient temperature
8: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
9: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
10: aq. HF / acetonitrile / 3 h / Ambient temperature
11: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: 56 mg / pivalic acid / toluene / 0.83 h / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-08-9

(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HF / acetonitrile / 3 h / Ambient temperature
2: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
1053614-44-0

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
2: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
3: aq. HF / acetonitrile / 3 h / Ambient temperature
4: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6-methoxy-2-{2-[(Z)-2-(6-methoxy-1H-indol-3-yl)-ethylimino]-ethyl}-cyclohexane-1,3-dicarboxylic acid dimethyl ester

(1S,2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6-methoxy-2-{2-[(Z)-2-(6-methoxy-1H-indol-3-yl)-ethylimino]-ethyl}-cyclohexane-1,3-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: pivalic acid / toluene / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-05-6

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aq. HF / acetonitrile / 0.5 h / Ambient temperature
2: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
3: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
4: aq. HF / acetonitrile / 3 h / Ambient temperature
5: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
1054654-18-0

(1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
2: aq. HF / acetonitrile / 3 h / Ambient temperature
3: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-02-3

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
2: aq. HF / acetonitrile / 0.5 h / Ambient temperature
3: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
4: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
5: aq. HF / acetonitrile / 3 h / Ambient temperature
6: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185810-98-4

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
2: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
3: aq. HF / acetonitrile / 0.5 h / Ambient temperature
4: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
5: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
6: aq. HF / acetonitrile / 3 h / Ambient temperature
7: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
reserpine
50-55-5

reserpine

methyl reserpate
2901-66-8

methyl reserpate

Conditions
ConditionsYield
With methanol; sodium methylate for 4h; Reflux;97%
With potassium hydroxide Hydrolysis;
With sodium methylate Hydrolysis;
Stage #1: reserpine With methanol; sodium methylate for 1h; Heating / reflux;
Stage #2: With hydrogenchloride; methanol; water pH=1;
Stage #3: With ammonia; water Product distribution / selectivity;
With sodium methylate In methanol for 1h; Heating / reflux;
reserpine
50-55-5

reserpine

methyl iodide
74-88-4

methyl iodide

N-methylreserpine
60634-65-3

N-methylreserpine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 2h;83%
reserpine
50-55-5

reserpine

(1S,4R,5aS,14bR,15aS,16R)-12,16-dimethoxy-4,5,5a,6,8,9,14,14b,15,15a-decahydro-1,4-methanoindolo[2,3-a]-oxepino[4,5-g]quinolizin-2(1H)-one
6811-42-3

(1S,4R,5aS,14bR,15aS,16R)-12,16-dimethoxy-4,5,5a,6,8,9,14,14b,15,15a-decahydro-1,4-methanoindolo[2,3-a]-oxepino[4,5-g]quinolizin-2(1H)-one

Conditions
ConditionsYield
With aluminum isopropoxide In xylene for 6h; Heating;81%
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;81%
With aluminum isopropoxide; xylene
reserpine
50-55-5

reserpine

reserpic acid lactone

reserpic acid lactone

Conditions
ConditionsYield
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;81%
reserpine
50-55-5

reserpine

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

(1S,2R,3R,4aS,13bR,14aS)-methyl-2,11-dimethoxy-13-(2-methylallyl)-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]-pyrido[1,2-b]isoquinoline-1-carboxylate

(1S,2R,3R,4aS,13bR,14aS)-methyl-2,11-dimethoxy-13-(2-methylallyl)-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]-pyrido[1,2-b]isoquinoline-1-carboxylate

Conditions
ConditionsYield
With titanium(IV) isopropylate; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; Inert atmosphere; Schlenk technique;66%
reserpine
50-55-5

reserpine

propargyl bromide
106-96-7

propargyl bromide

A

C36H42N2O9
1227009-31-5

C36H42N2O9

B

reserpine
1227009-32-6

reserpine

Conditions
ConditionsYield
Stage #1: reserpine With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.25h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at -20℃; for 1h;
A 30%
B 63%
reserpine
50-55-5

reserpine

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen; 1,5-Dichloroanthraquinone In acetonitrile at 20℃; for 2.5h; Sealed tube; Inert atmosphere; Irradiation;63%
reserpine
50-55-5

reserpine

11,17-dimethoxy-4-oxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester
474-48-6

11,17-dimethoxy-4-oxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide In acetone at 50℃; for 24h;60%
With monoperoxyphthalic acid
With Perbenzoic acid
reserpine
50-55-5

reserpine

allyl methyl carbonate
35466-83-2

allyl methyl carbonate

C36H44N2O9

C36H44N2O9

Conditions
ConditionsYield
Stage #1: allyl methyl carbonate With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane In dichloromethane at 20℃; Inert atmosphere;
Stage #2: reserpine In dichloromethane at 20℃; Inert atmosphere;
60%
reserpine
50-55-5

reserpine

butanoic acid anhydride
106-31-0

butanoic acid anhydride

A

10-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

12-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 56%
B 17%
reserpine
50-55-5

reserpine

propionyl chloride
79-03-8

propionyl chloride

A

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-propionyl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-propionyl-3β,20α-yohimban

B

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-propionyl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-propionyl-3β,20α-yohimban

C

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-propionyl-3β,20α-yohimban

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-propionyl-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 16%
B 56%
C 3%
reserpine
50-55-5

reserpine

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride In trifluoroacetic acid for 1h; Ambient temperature;55%
reserpine
50-55-5

reserpine

Hexanoyl chloride
142-61-0

Hexanoyl chloride

A

16β-carbomethoxy-10-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-10-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

16β-carbomethoxy-12-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-12-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 55%
B 16%
reserpine
50-55-5

reserpine

Heptanoic acid chloride
2528-61-2

Heptanoic acid chloride

A

16β-carbomethoxy-10-heptanoyl-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

16β-carbomethoxy-10-heptanoyl-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

B

16β-carbomethoxy-10-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-10-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

16β-carbomethoxy-12-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-12-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 2%
B 55%
C 18%
reserpine
50-55-5

reserpine

acetic anhydride
108-24-7

acetic anhydride

A

10-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

12-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

10,12-diacetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-3β,20α-yohimban

10,12-diacetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 54%
B 14%
C 2%
reserpine
50-55-5

reserpine

n-valeryl chloride
638-29-9

n-valeryl chloride

A

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-valeryl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-valeryl-3β,20α-yohimban

B

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-valeryl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-valeryl-3β,20α-yohimban

C

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-valeryl-3β,20α-yohimban

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-valeryl-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 51%
B 18%
C 4%
reserpine
50-55-5

reserpine

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

A

12-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

10-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

10-capryloyl-16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

10-capryloyl-16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 18%
B 50%
C 2%
reserpine
50-55-5

reserpine

methyl (1R,15S,17R,18R,19S,20S)-17-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyloxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate
21432-74-6

methyl (1R,15S,17R,18R,19S,20S)-17-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyloxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Conditions
ConditionsYield
Stage #1: reserpine With aluminum (III) chloride In dichloromethane for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;
47.1%
Stage #1: reserpine With aluminum (III) chloride In acetonitrile at 25℃; for 2h;
Stage #2: With hydrogenchloride In water; acetonitrile for 0.0833333h; Product distribution / selectivity;
22.4%
Stage #1: reserpine With aluminum tri-bromide In dichloromethane at 25℃; for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;
22.4%
reserpine
50-55-5

reserpine

A

hydroxyindolenine

hydroxyindolenine

B

7-hydroperoxy-7H-reserpine
127518-54-1

7-hydroperoxy-7H-reserpine

C

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen In acetonitrile for 2.5h; Irradiation; Inert atmosphere;A n/a
B n/a
C 46%
reserpine
50-55-5

reserpine

formaldehyd
50-00-0

formaldehyd

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-10,13-dimethyl-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-10,13-dimethyl-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride; trifluoroacetic acid In water at -5 - 20℃; for 0.75h; Mechanism; other indole alkaloids like tetraphylline, epireserpine, and reserpine; also AcOH as reagent; var. temp. and time;44.5%
With sodium cyanoborohydride; trifluoroacetic acid In water a) -5 deg C, 15 min, b) RT, 30 min;44.5%
reserpine
50-55-5

reserpine

formaldehyd
50-00-0

formaldehyd

7-2H-1,10-dimethyl-2,7-dihydroreserpine

7-2H-1,10-dimethyl-2,7-dihydroreserpine

Conditions
ConditionsYield
With trifluoroacetic acid-d1; sodium cyanoborohydride In water at 0℃; for 0.5h;42%
reserpine
50-55-5

reserpine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butyloxycarbonyl)reserpine
913379-66-5

N-(tert-butyloxycarbonyl)reserpine

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 12h;38%
reserpine
50-55-5

reserpine

A

Isoreserpin
482-85-9

Isoreserpin

B

(6aS,8R,9R,10S,10aS,11aS)-2-(2-Amino-4-methoxy-phenyl)-9-methoxy-8-(3,4,5-trimethoxy-benzoyloxy)-3,6,6a,7,8,9,10,10a,11,11a-decahydro-4H-pyrido[1,2-b]isoquinoline-10-carboxylic acid methyl ester
257622-17-6

(6aS,8R,9R,10S,10aS,11aS)-2-(2-Amino-4-methoxy-phenyl)-9-methoxy-8-(3,4,5-trimethoxy-benzoyloxy)-3,6,6a,7,8,9,10,10a,11,11a-decahydro-4H-pyrido[1,2-b]isoquinoline-10-carboxylic acid methyl ester

C

2,7-dihydroisoreserpine

2,7-dihydroisoreserpine

Conditions
ConditionsYield
With trifluoroacetic acid; zinc for 4h; Reduction; Heating;A 10%
B 15%
C 35%
reserpine
50-55-5

reserpine

para-tert-butylphenol
98-54-4

para-tert-butylphenol

N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

C56H67N3O12S

C56H67N3O12S

Conditions
ConditionsYield
In benzene at 85℃; for 16h; Diels-Alder Cycloaddition; Sealed tube; regioselective reaction;35%
reserpine
50-55-5

reserpine

A

7-hydroperoxy-7H-reserpine
127518-54-1

7-hydroperoxy-7H-reserpine

B

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen In chloroform for 360h; Mechanism; Ambient temperature; Irradiation; also with deuterated substrate;A 5.8%
B 28.1%
With oxygen In chloroform for 15h; Ambient temperature; Irradiation;A 5.8%
B 28.1%
With oxygen In chloroform for 2.5h; Inert atmosphere; Irradiation;
reserpine
50-55-5

reserpine

hydroxyindolenine

hydroxyindolenine

Conditions
ConditionsYield
Stage #1: reserpine With lead acetate In dichloromethane at 0℃; for 1.33333h; Inert atmosphere; Irradiation;
Stage #2: With sodium methylate In methanol at 0℃; for 2.5h; Inert atmosphere; Irradiation;
9%
reserpine
50-55-5

reserpine

Isoreserpin
482-85-9

Isoreserpin

Conditions
ConditionsYield
With acetic anhydride
With acetic acid; trichloroacetic acid
With trifluoroacetic acid epimerization; Heating;
With hydrogenchloride In methanol at 68℃; for 12h; Mechanism;280 mg
With hydrogenchloride In methanol for 72h; Heating;18 g
reserpine
50-55-5

reserpine

11,17-dimethoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimb-2-ene-16-carboxylic acid methyl ester

11,17-dimethoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimb-2-ene-16-carboxylic acid methyl ester

Conditions
ConditionsYield
With mercury(II) diacetate
With sodium nitrite
reserpine
50-55-5

reserpine

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; chloride
119720-94-4

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; chloride

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid Behandeln des Reaktionsprodukts mit wss.HCl;
reserpine
50-55-5

reserpine

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; perchlorate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; perchlorate

Conditions
ConditionsYield
With methanol; palladium; maleic acid Behandeln der Reaktionsloesung mit HClO4;

50-55-5Relevant articles and documents

A Desymmetrization-Based Total Synthesis of Reserpine

Park, Jisook,Chen, David Y.-K.

, p. 16152 - 16156 (2018/11/23)

Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.

COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE

-

, (2015/02/05)

To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.

Regiospecific and stereoselective syntheses of (±)-reserpine and (-)-reserpine

Stork, Gilbert,Tang, Peng Cho,Casey, Michael,Goodman, Burton,Toyota, Masahiro

, p. 16255 - 16262 (2007/10/03)

Full details of three approaches to an entirely regio- and Stereoselective synthesis of the well-known target reserpine are described, culminating in a total synthesis which efficiently meets these requirements.

Total synthesis of (-)-reserpine using the chiron approach

Hanessian, Stephen,Pan, Jingwen,Carnell, Andrew,Bouchard, Herve,Lesage, Luc

, p. 465 - 473 (2007/10/03)

A highly stereocontrolled synthesis of ring D/E precursor to reserpine has been developed starting from (-)-quinic acid as a chiral template. The total synthesis of (-)-reserpine is described through the cyclization of an immonium lactam intermediate.

Genaral Strategies for the Synthesis of Indole Alkaloids. Total Syntheses of (+/-)-Reserpine and (+/-)-α-Yohimbine

Martin, Stephen F.,Rueeger, Heinrich,Williamson, Sidney A.,Grzejszczak, Slawomir

, p. 6124 - 6134 (2007/10/02)

The concise, total syntheses of the indole alkaloids (+/-)-reserpine (1) and (+/-)-α-yohimbine (4) have been completed by the application of a general strategy that features an intramolecular Diels-Alder reaction for the facile construction of the functio

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 50-55-5