(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate → [1-(2-Chloro-quinolin-5-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester

HRID 651614Notes

Reaction equation

HRID 651614 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].Br[CH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([Cl:27])=[N:22]2.BrCC1C=C2C(C=CC(Cl)=N2)=CC=1.BrCC1C=C2C(C=CN=C2Cl)=CC=1>>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][C:21]([Cl:27])=[N:22]3)[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateHCID 113343577-Bromomethyl-2-chloro-quinolineHCID 114142025-Bromomethyl-2-chloro-quinolineHCID 181762527-(Bromomethyl)-1-chloroisoquinoline

Product 1

HCID 53882422[1-(2-Chloro-quinolin-5-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 1, Part H using a 2:1 mixture of 5-bromomethyl-2-chloro-quinoline to 7-bromomethyl-2-chloro-quinoline, as prepared in EXAMPLE 15, Part C, in place of 7-bromomethyl-1-chloro-isoquinoline. The crude product mixture is purified by column chromatography eluting with 1% MeOH in 25% EtOAc/CH2Cl2 to afford as the major product the title compound as a beige solid.

Workup

  1. customThe crude product mixture is purified by column chromatography
  2. washeluting with 1% MeOH in 25% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-9cc334e1ba284adabef1f5c73e2bd9c8
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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