L-Prolinol → (S)-N-(2-chlorobenzyl)-2-(hydroxymethyl)pyrrolidine-1-carboxamide

HRID 655961Notes

Reaction equation

HRID 655961 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][N:12]=[C:13]=[O:14]>C1COCC1>[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][NH:12][C:13]([N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7])=[O:14]

Participants

4

Reactant 2

HCID 640091L-ProlinolHCID 27333671-Chloro-2-(isocyanatomethyl)benzene

Product 1

HCID 59778476(S)-N-(2-chlorobenzyl)-2-(hydroxymethyl)pyrrolidine-1-carboxamideYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-pyrrolidin-2-ylmethanol (110 mg, 1.1 mmol) in THF (2.0 mL) was added 2-chlorobenzyl-isocyanate (167 mg, 1.0 mmol). The reaction mixture was stirred for 1 h and concentrated under reduced pressure to give (S)—N-(2-chlorobenzyl)-2-(hydroxymethyl)pyrrolidine-1-carboxamide as an oil (277 mg), which was used without further purification. LRMS (M+H+) m/z 269.0.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a991fe07ec824809a33d3c3ebc1dbca3
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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