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Technology Process of Usaramine

Usaramine

Base Information Edit
  • Chemical Name:Usaramine
  • CAS No.:15503-87-4
  • Molecular Formula:C18H25NO6
  • Molecular Weight:351.4
  • Hs Code.:
  • ChEMBL ID:CHEMBL520570
  • DSSTox Substance ID:DTXSID001020178
  • Nikkaji Number:J12.337D,J54.317I
  • Wikidata:Q27108514
  • Mol file:15503-87-4.mol
Usaramine

Synonyms:retrorsine;retrorsine hydrochloride;retrorsine, (15E)-isomer;usaramine

Suppliers and Price of Usaramine
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • ChemScene
  • Usaramine
  • 10mg
  • $ 571.00
  • ChemScene
  • Usaramine
  • 5mg
  • $ 336.00
  • AvaChem
  • Usaramine
  • 20mg
  • $ 269.00
  • AvaChem
  • Usaramine
  • 5mg
  • $ 139.00
  • Arctom
  • Usaramine ≥98%
  • 5mg
  • $ 318.00
  • Arctom
  • Usaramine;mucronatine 95%
  • 5mg
  • $ 87.00
  • ApexBio Technology
  • Usaramine
  • 20mg
  • $ 400.00
Total 28 raw suppliers
Chemical Property of Usaramine Edit
Chemical Property:
  • Melting Point:178-180℃ 
  • Boiling Point:583.2°Cat760mmHg 
  • PKA:12.00±0.40(Predicted) 
  • Flash Point:306.5°C 
  • PSA：96.30000 
  • Density:1.32g/cm3 
  • LogP:0.10310 
  • XLogP3:0.6
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:7
  • Rotatable Bond Count:1
  • Exact Mass:351.16818752
  • Heavy Atom Count:25
  • Complexity:627
Purity/Quality:

≥98% *data from raw suppliers

Usaramine *data from reagent suppliers

Safty Information:
  • Pictogram(s): A poison. 
  • Hazard Codes: A poison.:;
     
  • Safety Statements:A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.:;"> x." target="_blank">A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.:; 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O)C
  • Isomeric SMILES:C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C
  • Description A pyrrolizidine alkaloid first isolated from Crotalaria usararnoensis E. G. Baker, this base has more recently been found in C. brevifolia and C. rnucronata. The alkaloid has [α]20D + 6.1° (c 0.38, EtOH) or + 7.1° (c 1.83, EtOH). It yields a picrate, m.p. 230- 2°C (dec.); picrolonate, m.p. 148-150°C (dec.); reineckate, m.p. 190-2°C (dec.) and methiodide, m.p. 229-230°C (dec.). Alkaline hydrolysis furnishes retronecine and retronecic acid, m.p. 177-9°C. It has been suggested that the base may be identical with Mucronatine (q.v.).
Technology Process of Usaramine

There total 26 articles about Usaramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-Citronellal
2385-77-5

(R)-Citronellal

usaramine
15503-87-4

usaramine

Guidance literature:
Multi-step reaction with 22 steps
1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 45 min, 2a) THF, -78 deg C, 45 min, 2b) r.t., 5 h
2: 1) MeI, 2) 5 percent aq. NaHCO3 / 1a) MeOH, 4 deg C, overnight, 1b) r.t., 5 h, 2) CH2Cl2, r.t., 16 h
3: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min
4: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight
5: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h
6: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h
7: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating
8: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature
9: 99 percent / diethyl ether
10: 93 percent / Ti(OEt)4 / 60 h / 100 °C
11: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h
12: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7
13: 96 percent / HOAc / H2O / 8 h / 75 °C
14: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h
15: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C
16: 1) N-isopropylcyclohexylamine, n-BuLi / 1) THF, hexane, -60 to -50 deg C, 45 min, 2a) -60 deg C, 45 min, 2b) to -20 deg C, 10 min
17: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h
18: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C
19: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h
20: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h
21: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature
With titanium(IV) isopropylate; hydrogenchloride; dmap; ruthenium trichloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; (-)-diisopropyl tartrate; dimethylsulfide; Cumene hydroperoxide; MS 3 Angstroem; N-cyclohexylisopropylamine; camphor-10-sulfonic acid; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; sodium hydrogencarbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00034a017

Reference yield:

(3R)-citronellol
1117-61-9

(3R)-citronellol

usaramine
15503-87-4

usaramine

Guidance literature:
Multi-step reaction with 23 steps
1: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h
2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 45 min, 2a) THF, -78 deg C, 45 min, 2b) r.t., 5 h
3: 1) MeI, 2) 5 percent aq. NaHCO3 / 1a) MeOH, 4 deg C, overnight, 1b) r.t., 5 h, 2) CH2Cl2, r.t., 16 h
4: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min
5: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight
6: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h
7: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h
8: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating
9: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature
10: 99 percent / diethyl ether
11: 93 percent / Ti(OEt)4 / 60 h / 100 °C
12: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h
13: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7
14: 96 percent / HOAc / H2O / 8 h / 75 °C
15: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h
16: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C
17: 1) N-isopropylcyclohexylamine, n-BuLi / 1) THF, hexane, -60 to -50 deg C, 45 min, 2a) -60 deg C, 45 min, 2b) to -20 deg C, 10 min
18: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h
19: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C
20: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h
21: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h
22: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature
With titanium(IV) isopropylate; hydrogenchloride; dmap; ruthenium trichloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; (-)-diisopropyl tartrate; dimethylsulfide; Cumene hydroperoxide; MS 3 Angstroem; N-cyclohexylisopropylamine; camphor-10-sulfonic acid; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00034a017

Reference yield:

(R)-citronellic acid
18951-85-4,57030-77-0

(R)-citronellic acid

usaramine
15503-87-4

usaramine

Guidance literature:
Multi-step reaction with 24 steps
1: 97 percent / LiAlH4 / diethyl ether / 0 °C
2: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h
3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 45 min, 2a) THF, -78 deg C, 45 min, 2b) r.t., 5 h
4: 1) MeI, 2) 5 percent aq. NaHCO3 / 1a) MeOH, 4 deg C, overnight, 1b) r.t., 5 h, 2) CH2Cl2, r.t., 16 h
5: 95 percent / CeCl3*6H2O, NaBH4 / methanol / 0 °C / 5 to 10 min
6: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH2Cl2, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight
7: 51 percent / Ti(O-i-Pr)4 / benzene / 0.33 h
8: 98 percent / camphorsulfonic acid / CH2Cl2 / 5 h
9: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating
10: 67 percent / pyridinium dichromate / dimethylformamide / 30 h / Ambient temperature
11: 99 percent / diethyl ether
12: 93 percent / Ti(OEt)4 / 60 h / 100 °C
13: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 45 min, 2) to r.t., 7 h
14: 67 percent / NaIO4, 2 percent RuCl3*3H2O / acetonitrile; CCl4 / 0.33 h / Ambient temperature; phosphate buffer, pH 7
15: 96 percent / HOAc / H2O / 8 h / 75 °C
16: 74 percent / 2-chloro-1-methylpyridinium iodide, 4-(dimethylamino)pyridine / acetonitrile / a) 0 deg C, 3 h, b) r.t., 10 h
17: 91 percent / (i-Pr)2NEt / tetrahydrofuran / 15 h / 50 °C
18: 1) N-isopropylcyclohexylamine, n-BuLi / 1) THF, hexane, -60 to -50 deg C, 45 min, 2a) -60 deg C, 45 min, 2b) to -20 deg C, 10 min
19: Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h
20: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 15 h / 4 °C
21: 90 percent / 3 M aq. HCl / tetrahydrofuran / a) r.t., 1 h, b) 35 deg C, 10 h
22: 60 percent / RuCl3*3H2O, 30 percent aq. H2O2 / tetrahydrofuran / a) 0 deg C, 0.5 h, b) r.t., 2 h
23: 91 percent / camphorsulfonic acid / CHCl3 / 12 h / Ambient temperature
With titanium(IV) isopropylate; hydrogenchloride; dmap; ruthenium trichloride; titanium(IV) tetraethanolate; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; (-)-diisopropyl tartrate; dimethylsulfide; Cumene hydroperoxide; MS 3 Angstroem; N-cyclohexylisopropylamine; camphor-10-sulfonic acid; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00034a017
upstream raw materials:

9-O-(tert-Butyldimethylsilyl)retronecine

(S)-4-((E)-(R)-3-Carboxy-1-methyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

(R)-Citronellal

(3R)-citronellol

Downstream raw materials:

retronecine pyrrole

retronecic acid

retrorsine

Refernces Edit

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