(1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide

Base Information

• Chemical Name: (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide
• CAS No.: 225791-07-1
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.283
• Mol file: 225791-07-1.mol

Synonyms:(1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide

Chemical Property of (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide

There total 3 articles about (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide 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: 85.0%

N-benzyl-2-oxocyclopentane-1-carboxamide (2799-86-2) → (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide (225791-07-1) + (1S,2S)-trans-N-benzyl-2-hydroxycyclopentanecarboxamide

Guidance literature:

In ethanol; at 28 ℃; for 24h; fungus Mortierella isabellina NRRL 1757;

DOI:10.1016/S0957-4166(99)00016-6

Reference yield:

Cyclopentene oxide (285-67-6) → C13H17NO2 + (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide (225791-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); dicobalt octacarbonyl / 1,2-dimethoxyethane / 16 h / 70 °C / 1034.32 - 25858.1 Torr / Inert atmosphere

2: tetrahydrofuran / 20 °C / Inert atmosphere

With dicobalt octacarbonyl; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1039/c2cc35596e

Reference yield:

6-oxabicyclo[3.2.0]heptan-7-one (864365-92-4) + benzylamine (100-46-9) → C13H17NO2 + (1R,2S)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide (225791-07-1)

Guidance literature:

In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1039/c2cc35596e

upstream raw materials:

N-benzyl-2-oxocyclopentane-1-carboxamide

6-oxabicyclo[3.2.0]heptan-7-one

benzylamine

Cyclopentene oxide

Downstream raw materials:

(1S,2S)-cis-2-(N-benzylaminomethyl)cyclopentanol