2-Chloro-4-isocyanato-3-methylbenzonitrile → (2R,3S)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1864697Notes

Reaction equation

HRID 1864697 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@:9]1([CH2:22][OH:23])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C(C)=C(N=C=O)C=CC=1C#N>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@:9]1([CH2:22][OH:23])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 167318492-Chloro-4-isocyanato-3-methylbenzonitrileHCID 69019276(2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 59754210(2R,3S)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic Acid Tert-Butyl EsterYield 68.9%

Procedure

Compound 4D (84.0 mg) was prepared from compound 4C (122 mg) and compound 1G (82.0 mg) following procedures analogous to those used in Example 1 for the preparation of compound 1H. LCMS: m/z 438 [M+H]+.

Sources & evidence

ORD record
ord-312d365331d84c9a94a033dcd6674f94
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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