4-(Bromomethyl)picolinonitrile → [1-(2-Cyano-pyridin-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]carbamic acid tert-butyl ester

HRID 619856Notes

Reaction equation

HRID 619856 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13])([CH3:4])([CH3:3])[CH3:2].[C:15]([C:17]1[CH:22]=[C:21]([CH2:23]Br)[CH:20]=[CH:19][N:18]=1)#[N:16]>>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH2:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([C:15]#[N:16])[CH:22]=2)[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 106317764-(Bromomethyl)picolinonitrileHCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

Product 1

HCID 10829192[1-(2-Cyano-pyridin-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]carbamic acid tert-butyl ester

Procedure

The title compound is prepared from (2-oxopyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester as described in EXAMPLE 122, Part F using 2-cyano-4-(bromomethyl)pyridine in place of 4-bromomethylthiophene-2-carbonitrile. The crude product is purified by column chromatography eluting with gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2 to afford the title compound as a solid.

Workup

  1. customThe crude product is purified by column chromatography
  2. washeluting with gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b8c89eeff8dc46c5a1678e149c6cb36a
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

Loading…