N-(4-Isopropylphenyl)carbamic acid (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester

Base Information

• Chemical Name: N-(4-Isopropylphenyl)carbamic acid (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester
• CAS No.: 219920-81-7
• Molecular Formula: C₂₁H₂₅N₃O₂
• Molecular Weight: 351.448
• Mol file: 219920-81-7.mol

Synonyms:(-)-N¹,N⁸-bisnorcymserine

Chemical Property of N-(4-Isopropylphenyl)carbamic acid (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-Isopropylphenyl)carbamic acid (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester

There total 7 articles about N-(4-Isopropylphenyl)carbamic acid (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester 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: 70.0%

N1-benzyl-N8-norcymserine (290294-30-3) → (-)-N1,N8-bisnorcymserine (219920-81-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In isopropyl alcohol;

DOI:10.1016/S0040-4039(00)00740-1

Reference yield:

eseroline (469-22-7) → (-)-N1,N8-bisnorcymserine (219920-81-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / KOH / dimethylsulfoxide

2: 19 percent / pyridinium dichromate; NaHCO₃ / CH₂Cl₂ / 2 h / ice-bath

3: 85 percent / sodium borohydride / tetrahydrofuran

4: 97 percent / Na / diethyl ether

5: 70 percent / H₂ / Pd(OH)2/C / propan-2-ol

With potassium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; hydrogen; sodium; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; 1: Methylation / 1: Substitution / 2: Oxidation / 3: Reduction / 4: Condensation / 5: Hydrogenolysis;

DOI:10.1016/S0040-4039(00)00740-1

Reference yield:

(-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole (116103-15-2) → (-)-N1,N8-bisnorcymserine (219920-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 19 percent / pyridinium dichromate; NaHCO₃ / CH₂Cl₂ / 2 h / ice-bath

2: 85 percent / sodium borohydride / tetrahydrofuran

3: 97 percent / Na / diethyl ether

4: 70 percent / H₂ / Pd(OH)2/C / propan-2-ol

With sodium tetrahydroborate; dipyridinium dichromate; hydrogen; sodium; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; 1: Oxidation / 2: Reduction / 3: Condensation / 4: Hydrogenolysis;

DOI:10.1016/S0040-4039(00)00740-1

upstream raw materials:

N₁-benzyl-N₈-norcymserine

4-isopropylphenylisocyanate

(-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole

eseroline

Refernces

• 1、 Zhu, Xiaoxiang,Greig, Nigel H.,Holloway, Harold W.,Whittaker, Noel F.,Brossi, Arnold,Yu, Qian-Sheng. "A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine". . p. 4861 - 4864. Retrieved 2007/10/03.