(+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate
• CAS No.: 1295650-27-9
• Molecular Formula: C₂₅H₂₈ClNO₃
• Molecular Weight: 425.955
• Mol file: 1295650-27-9.mol

Synonyms:

Chemical Property of (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate

There total 4 articles about (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate 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:

methyl (+)-(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylate (290341-74-1) + (3-endo)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]octan-3-ol (637311-69-4) → (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate (1295650-27-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 60 ℃; for 6h;

DOI:10.1021/jm200144j

Reference yield:

bromochlorobenzene (106-39-8) → (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate (1295650-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -70 °C / Inert atmosphere

1.2: 2 h / -70 - -50 °C / Inert atmosphere

2.1: carbonochloridic acid 1-chloro-ethyl ester / 1,2-dichloro-ethane / 48 h / Inert atmosphere; Reflux

3.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 6 h / 60 °C

With n-butyllithium; carbonochloridic acid 1-chloro-ethyl ester; sodium hydrogencarbonate; In tetrahydrofuran; hexane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm200144j

Reference yield:

(3-endo)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol (22932-27-0) → (+)-methyl (1R,2S)-2-{[(3-endo)-3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-1-phenylcyclopropanecarboxylate (1295650-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: carbonochloridic acid 1-chloro-ethyl ester / 1,2-dichloro-ethane / 48 h / Inert atmosphere; Reflux

2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 6 h / 60 °C

With carbonochloridic acid 1-chloro-ethyl ester; sodium hydrogencarbonate; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm200144j

upstream raw materials:

bromochlorobenzene

(3-endo)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

tropinone

methyl (+)-(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylate