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1617-90-9

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1617-90-9 Usage

Chemical Properties

white to almost white fine crystalline powder

Originator

Pervancamine ,Dausse,France,1969

Uses

Different sources of media describe the Uses of 1617-90-9 differently. You can refer to the following data:
1. Vincamine is often used as a nootropic agent to combat the effects of aging, or in conjunction with other nootropics (such as piracetam) for a variety of purposes. Vincamine is a peripheral vasodilator that increases blood flow to the brain.
2. vasodilator

Manufacturing Process

The following route is described in US Patent 4,145,552: At ambient temperature, over a period of thirty minutes, a solution of 33.8g (0.1mol) of (-)-vincadiformine in a mixture of 140 ml of anhydrous dimethylformamide and 140 ml of anhydrous toluene is added to a suspension of 2.64 g (0.11 mol) of sodium hydride in a mixture of 200 ml of anhydrous tetrahydrofuran, 20 ml of anhydrous hexamethylphosphotriamide (EMPT) and 18.7 ml (0.14 mol) of trimethyl phosphite. When the release of hydrogen has finished (about two hours later), the solution is cooled to -10°C and then stirred under an oxygen atmosphere until absorption ceases (duration: 3 hours). Still at -10°C, 136 ml of glacial acetic acid are added, and the mixture is then left at ambient temperature for two hours. After the addition of 500 ml of 1 N sulfuric acid, the aqueous phase is isolated, reextracted with 150 ml of isopropyl ether, made alkaline with 350 ml of 11 N ammonia, then extracted 3 times with 300 ml aliquots of methylene chloride. After drying over calcium chloride and evaporating the solvent, 30.2 g of crude product are obtained which, when chromatographed on a column of silica gel (1.5 kg) yield, 9.9 g of vincamine (yield: 28%) melting point (decomp.): 250°C.

Brand name

Cerebroxine;Cetal;Ocu-vinc;Oxygeron;Pervincamine;Vadicate;Vinca minor;Vincacen;Vincapront;Vincavix;Vincimax.

Therapeutic Function

Vasodilator

World Health Organization (WHO)

Vincamine, an alkaloid derived from Vinca minor, is claimed to increase cerebral circulation and utilization of oxygen. It is used in a variety of cerebral disorders and is widely marketed for this purpose.

General Description

Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor L., belonging to the Apocynaceae family.

Check Digit Verification of cas no

The CAS Registry Mumber 1617-90-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,1 and 7 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1617-90:
(6*1)+(5*6)+(4*1)+(3*7)+(2*9)+(1*0)=79
79 % 10 = 9
So 1617-90-9 is a valid CAS Registry Number.
InChI:InChI=1/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/p+1/t18-,20+,21+/m1/s1

1617-90-9 Well-known Company Product Price

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

  • (V0061)  Vincamine  >98.0%(T)

  • 1617-90-9

  • 1g

  • 555.00CNY

  • Detail
  • TCI America

  • (V0061)  Vincamine  >98.0%(T)

  • 1617-90-9

  • 5g

  • 1,850.00CNY

  • Detail
  • Sigma-Aldrich

  • (75778)  Vincamine  analytical reference material

  • 1617-90-9

  • 75778-50MG

  • 916.11CNY

  • Detail

1617-90-9Synthetic route

(+)-15α-Chloro-vincamine
142892-63-5

(+)-15α-Chloro-vincamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal In methanol for 6h; Ambient temperature;84.7%
14-epivincamine
6835-99-0

14-epivincamine

A

vincamin
1617-90-9

vincamin

B

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
at 250℃; for 0.25h;A 7%
B 83%
at 20℃; for 0.25h;A 8%
B 75%
(-)-vincadifformine
3247-10-7

(-)-vincadifformine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Stage #1: (-)-vincadifformine With monoperoxymaleic acid In methanol at -5 - 0℃; for 6.16667h;
Stage #2: With sodium dithionate at 40℃; for 3h; Reagent/catalyst;
78.3%
hydroxy-16 dehydro-1 vincadifformine
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

vincamin
1617-90-9

vincamin

B

vinburnine
4880-88-0

vinburnine

Conditions
ConditionsYield
In toluene at 450℃; under 20 Torr;A 5%
B 70%
O-methyl vincamine
96861-85-7

O-methyl vincamine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride In acetone for 72h; Ambient temperature; Yields of byproduct given;A n/a
B 66%
(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime
85588-92-7

(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium disulfite; acetic acid In water at 90 - 92℃; for 6h; Yields of byproduct given;A n/a
B 60%
With sodium disulfite; acetic acid In water at 90 - 92℃; for 6h; Yield given. Title compound not separated from byproducts;A n/a
B 60%
With sodium disulfite; acetic acid In water at 92 - 95℃; for 5h;A 20%
B 40%
hydroxy-16 dehydro-1 vincadifformine
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
at 150℃; for 0.25h;A 35%
B 60%
at 150℃; for 0.25h; other condition;A 35%
B 60%
In acetic acid at 20℃; for 12h;A 4 mg
B 50 mg
In acetic acid for 12h; Ambient temperature;A 4 mg
B 50 mg
dichloromethane
75-09-2

dichloromethane

MCPB
94-81-5

MCPB

potassium carbonate
584-08-7

potassium carbonate

A

methyl 3-benzyl-4,4-diethyl-6-hydroxy-2,3,3,a4,5,6-hexahydro-1H-indolo(3,2,1-de)(1,5)naphthyridine-6-carboxylate

methyl 3-benzyl-4,4-diethyl-6-hydroxy-2,3,3,a4,5,6-hexahydro-1H-indolo(3,2,1-de)(1,5)naphthyridine-6-carboxylate

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; ammonia; sodium chloride In methanolA n/a
B 58%
14-epivincamine
6835-99-0

14-epivincamine

A

vincamin
1617-90-9

vincamin

B

vinburnine
4880-88-0

vinburnine

C

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
In toluene at 400℃; under 20 Torr;A 9%
B 47%
C 10%
(-)-vincadifformine
3247-10-7

(-)-vincadifformine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium hydroxide; oxygen; sodium acetate; rose bengal; sodium thiosulfate; acetic acid 1.) methanol, irradation, 60 min, 2.) H2O, 70 deg C, 20 min; Yield given. Multistep reaction;A n/a
B 46%
With sodium hydroxide; oxygen; sodium acetate; rose bengal; sodium thiosulfate; acetic acid 1.) methanol, irradation, 60 min, 2.) H2O; Yield given. Multistep reaction. Yields of byproduct given;
With sulfuric acid; ozone In methanol at 60℃; Yield given. Yields of byproduct given;
methanol
67-56-1

methanol

(3α,16α)-D-homoeburnamonine-14,15-dione
35226-43-8

(3α,16α)-D-homoeburnamonine-14,15-dione

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With potassium tert-butylate at 20℃; for 2h;40%
With potassium tert-butylate for 2h; Ambient temperature;
(-)-vincadifformine hydrochloride

(-)-vincadifformine hydrochloride

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

C

C21H26N2O4
78084-15-8

C21H26N2O4

Conditions
ConditionsYield
With methylene blue In methanol for 4h; Irradiation;A 2 mg
B 10 mg
C 40%
(-)-2-(1α-Ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizin-1-yl)-2-oxoacetic acid
100945-10-6, 100992-96-9, 120201-19-6

(-)-2-(1α-Ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizin-1-yl)-2-oxoacetic acid

A

vincamin
1617-90-9

vincamin

B

(-)-14-oxo-15α-oxirano-eburnane
120090-43-9

(-)-14-oxo-15α-oxirano-eburnane

Conditions
ConditionsYield
In methanol; dichloromethane at 0℃; for 4h; Product distribution; reactions of vincamones and eburnanes;A 38%
B 27%
In methanol; dichloromethane at 0℃; for 4h;A 32%
B 27%
3-((1S,12bS)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester
89396-77-0

3-((1S,12bS)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester

A

vincamin
1617-90-9

vincamin

B

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
With sulfuric acid; sodium methylate 1.) AcOH, heating, 2 h; 2.) MeOH, rt, 2 h; Yield given. Multistep reaction;A n/a
B 35%
(+)-15,15a-didehydro-15-formamido-D-homoeburnamin-14-one
112965-87-4

(+)-15,15a-didehydro-15-formamido-D-homoeburnamin-14-one

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; acetyl chloride for 4h; Heating; Yield given. Yields of byproduct given;
methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate
83289-24-1

methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate

(+/-)-16-epi vincamine
18210-81-6

(+/-)-16-epi vincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temp., 30 min; Yield given. Multistep reaction. Title compound not separated from byproducts;
methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate
83289-24-1

methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
14-epivincamine
6835-99-0

14-epivincamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 4h; Equilibrium constant; Rate constant; Heating;
14-iodo criocerine
74947-45-8

14-iodo criocerine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium cyanoborohydride In acetic acid at 20℃; for 2.5h;8 mg
(1S,12bS,2'S)-1α-ethyl-1β-(2-hydroxy-2-methoxycarbonylethyl)-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine
25328-05-6, 25819-96-9, 34786-67-9, 41173-96-0, 55528-20-6, 64395-18-2, 65634-79-9, 65634-80-2, 95782-87-9

(1S,12bS,2'S)-1α-ethyl-1β-(2-hydroxy-2-methoxycarbonylethyl)-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium methylate 1.) toluene, reflux, 6 h; 2.) MeOH, reflux, 1 h; Yield given. Multistep reaction;
Δ14-vincamine
32790-09-3

Δ14-vincamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol9 mg
Multi-step reaction with 2 steps
1: 49 mg / acetic acid, iodine, potassium iodate / dioxane / 24 h / 20 °C
2: 8 mg / NaBH3CN / acetic acid / 2.5 h / 20 °C
View Scheme
tryptamine
61-54-1

tryptamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 83 percent / tetrahydrofuran / 12 h / 20 °C
2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
4: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
5: p-TsOH / toluene / 12 h / Heating
6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
7: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
8: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
9: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
10: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
11: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
12: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
13: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 19 steps
1: 83 percent / tetrahydrofuran / 12 h / 20 °C
2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
4: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
5: p-TsOH / toluene / 12 h / Heating
6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
7: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
8: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
9: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
10: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
11: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
12: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
13: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
14: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
15: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
16: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
17: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
18: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
19: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester
14487-98-0

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
2: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
3: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
4: p-TsOH / toluene / 12 h / Heating
5: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
6: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
7: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
8: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
9: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
10: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
11: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
12: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 18 steps
1: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
2: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
3: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
4: p-TsOH / toluene / 12 h / Heating
5: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
6: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
7: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
8: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
9: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
10: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
11: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
12: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
13: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
14: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
15: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
16: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
17: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
18: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
(-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine
23944-42-5

(-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
2: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
3: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
4: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tert-butyl nitrite, potassium tert-butoxide / toluene; methanol / 3 h / 40 °C
2: 40 percent / acetic acid, sodium disulfite / H2O / 5 h / 92 - 95 °C
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / NaOH / aq. ethanol / 1.5 h / Heating
2: 77 percent / phosphoryl chloride / 24 h / Ambient temperature
3: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
4: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
5: t-BuOK / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 60 percent / NaH / toluene / 5 h / Heating
2: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
3: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
4: t-BuOK / 2 h / Ambient temperature
View Scheme
(+)-(3S,17S)-14-oxo-E-homo-eburnane
35226-41-6

(+)-(3S,17S)-14-oxo-E-homo-eburnane

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
2: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
3: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
2: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
3: t-BuOK / 2 h / Ambient temperature
View Scheme
15a-homo-eburnamenine-14,15-dione 15-oxime
35226-42-7

15a-homo-eburnamenine-14,15-dione 15-oxime

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
2: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-2,4-piperidinedione
190378-04-2

3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-2,4-piperidinedione

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: p-TsOH / toluene / 12 h / Heating
2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
3: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
4: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
5: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
6: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
7: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
8: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
9: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 15 steps
1: p-TsOH / toluene / 12 h / Heating
2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
3: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
4: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
5: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
6: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
7: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
8: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
9: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
10: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
11: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
12: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
13: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
14: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
15: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
vincamin
1617-90-9

vincamin

(15S,17S,19S)-15-ethyl-17-(hydroxymethyl)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol
3382-95-4

(15S,17S,19S)-15-ethyl-17-(hydroxymethyl)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 1.5h; Inert atmosphere;99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 1.5h; Inert atmosphere;99%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 2.5h;51%
vincamin
1617-90-9

vincamin

2,7-seco 14-epivincamine
59373-44-3

2,7-seco 14-epivincamine

Conditions
ConditionsYield
With 3,7-bis(dimethylamino)phenothiazin-5-ium chloride trihydrate; oxygen In methanol Irradiation;99%
With oxygen; methylene blue for 24h; Irradiation;35%
vincamin
1617-90-9

vincamin

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 2h; Dean-Stark; Reflux; Inert atmosphere;95%
With toluene-4-sulfonic acid In toluene for 2h; Reflux;92%
With toluene-4-sulfonic acid In toluene for 2h; Reflux;92%
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester
40163-56-2

14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester

Conditions
ConditionsYield
With titanium(IV) tetraethanolate In various solvent(s) for 8h; Heating;90%
vincamin
1617-90-9

vincamin

(-)-vincamine N-oxide
51442-60-5, 1239866-77-3

(-)-vincamine N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform84.8%
propan-1-ol
71-23-8

propan-1-ol

vincamin
1617-90-9

vincamin

(41S,13aS)-propyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

(41S,13aS)-propyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 8h; Reflux;81%
With sulfuric acid for 8h; Reflux;81%
methanol
67-56-1

methanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl 7-ethyl-14-hydroxy-8-methoxy-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1,2,3,4,5,6,7,8-octahydro-7,9-ethanoazecino[5,4-b]indole-14-carboxylate

methyl 7-ethyl-14-hydroxy-8-methoxy-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1,2,3,4,5,6,7,8-octahydro-7,9-ethanoazecino[5,4-b]indole-14-carboxylate

Conditions
ConditionsYield
Reflux;78%
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

A

C27H36N2O6

C27H36N2O6

B

C27H36N2O6

C27H36N2O6

Conditions
ConditionsYield
In tetrahydrofuran at 66℃; for 3.5h; Inert atmosphere;A 78%
B 15%
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

A

methyl (9R,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

methyl (9R,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

B

methyl (9S,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

methyl (9S,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

Conditions
ConditionsYield
In chloroform at 62℃; for 4h; Inert atmosphere; diastereoselective reaction;A 15%
B 78%
vincamin
1617-90-9

vincamin

(-)-18-iodo-criocerine
74947-45-8

(-)-18-iodo-criocerine

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate In chloroform for 2h; Ambient temperature;77%
With iodine; sodium hydrogencarbonate In chloroform at 20℃;77%
With iodine; sodium hydrogencarbonate In chloroform; water for 6h; Inert atmosphere;77%
vincamin
1617-90-9

vincamin

n-butyl isocyanide
111-36-4

n-butyl isocyanide

(3S,14S,16S)-eburnane-14-spiro-5'-(3'-butyloxazolidine-2',4'-dione)

(3S,14S,16S)-eburnane-14-spiro-5'-(3'-butyloxazolidine-2',4'-dione)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 4h;75%
vincamin
1617-90-9

vincamin

isopropyl alcohol
67-63-0

isopropyl alcohol

(41S,13aS)-isopropyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

(41S,13aS)-isopropyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 8h; Reflux;74%

1617-90-9Related news

Zafirlukast and Vincamine (cas 1617-90-9) ameliorate tamoxifen-induced oxidative stress and inflammation: Role of the JNK/ERK pathway07/20/2019

AimsThis study investigated the hepatoprotective effects of both zafirlukast and vincamine and their possible role in the treatment of tamoxifen-induced liver injury in rats.detailed

Vincamine (cas 1617-90-9) and 14-epi-Vincamine (cas 1617-90-9) indole alkaloids from Ambelania occidentalis07/21/2019

Two indole alkaloids, Vincamine 1 and 14-epi-vincamine 2 were isolated here for the first time from Ambelania occidentalis. The structures of these compounds were elucidated by one and two dimension NMR and MS spectroscopy.detailed

1617-90-9Relevant articles and documents

Ozonation in Alkaloid Chemistry: a Mild and Selective Conversion of Vincadifformine into Vincamine

Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni,Gabetta, Bruno

, p. 908 - 909 (1981)

Vincamine has been obtained in a 'one-pot' method by ozonation of vincadifformine.

SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS. PART 18. STEREOCHEMICAL INVESTIGATIONS ON SOME INTERMEDIATES LEADING TO (+)-VINCAMINE

Szabo, Lajos,Kolonits, Pal,Kalaus, Gyoergy,Szantay, Csaba,Kalman, Alajos,et al.

, p. 1629 - 1636 (1984)

The C-2' absolute configrations of hydroxy esters (1) and (2) have been determined by X-ray analysis.The absolute configurations at C-15 of several compounds with the E-homoeburnane skeleton and the relative configurations at C-14 and -15 of compound (8) have been elucidated.The dominant conformation of compounds (3)-(7) have been established on the basis of 13C n.m.r. and c.d.spectroscopic results.A new method has been elaborated for the preparation of oxime (10), a compound of importance in the synthesis of Vinca alkaloids.

Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora

Koyama, Koichiro,Hirasawa, Yusuke,Hosoya, Takahiro,Hoe, Teh Chin,Chan, Kit-Lam,Morita, Hiroshi

, p. 4415 - 4421 (2010)

Eight new indole alkaloids, alpneumines A-H (1-8) were isolated from the Malaysian Alstonia pneumatophora (Apocynaceae) and their structures were determined by MS and 2D NMR spectroscopic methods. Alpneumines E and G (5 and 7), vincamine, and apovincamine showed anti-melanogenesis in B16 mouse melanoma cells.

Kuehne

, p. 2946 (1964)

Synthesis of vinca alkaloids and related compounds LX. A simple transformation of apovincamine into vincamine

Moldvai, Istvan,Szantay Jr., Csaba,Rissanen, Kari,Szantay, Csaba

, p. 4999 - 5008 (1992)

The 15α-chloro-vincamine derivative 2 was prepared and proved to be key intermediate of a two-step transformation of apovincamine into vincamine. The structure of 2 was established via detailed NMR and X-ray investigations.

Intermediate, preparation method and application of intermediate in synthesis of vincamine

-

, (2021/09/01)

The invention relates to the technical field of chemical drug synthesis, and discloses an intermediate, a preparation method and application of the intermediate in synthesis of vincamine. A modular synthesis strategy is adopted, and a compound 1 with a D ring structure and a C20 quaternary carbon center and a tryptophol derivative 7 (namely the compound 7) with an indole ring are adopted as synthesis blocks for synthesis. The synthesis method is efficient; each step of the synthesis route is simple in reaction; the used reagent and solvent are cheap and easy to obtain; the operation is simple and convenient; the yield is high; and large-scale production is easy.

Preparation method of high-purity vinpocetine (by machine translation)

-

Paragraph 0041; 0043-0044; 0051-0056, (2020/04/17)

The preparation method, of the high-purity vinpocetine :S1. comprises, following steps: preparing vinpocstine, by dissolving; in toluene as a solvent; in toluene as a solvent ;S2. and carrying out an ester exchange reaction, to obtain the intermediate vinpocstine nitrogen oxide, in a toluene as a solvent, and carrying out an ester exchange reaction to obtain a product impurity at least ;S3. purity S2 and, % by mass of a solvent . The preparation method of the vinpocstine nitrogen oxide reaction solution in step, is adopted as a catalyst for carrying out an ester exchange reaction to obtain a long spring cavoniflorac sodium/vinpocstine . The process production operation is, simple, avoids the high, 99.9% toxicity reagent, to obtain a, long spring cavonift, nitrogen oxide reaction, solution to, obtain a product, impurity at a time of acid. (by machine translation)

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