(R)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate → [1-(1-Chloroisoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(R)-yl]carbamic acid tert-butyl ester

HRID 651688Notes

Reaction equation

HRID 651688 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]=[C:25]2[C:20]([CH:21]=[CH:22][N:23]=[C:24]2[Cl:27])=[CH:19][CH:18]=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]=[C:25]3[C:20]([CH:21]=[CH:22][N:23]=[C:24]3[Cl:27])=[CH:19][CH:18]=2)[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 10774403(R)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateHCID 181762527-(Bromomethyl)-1-chloroisoquinoline

Product 1

HCID 86757283[1-(1-Chloroisoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(R)-yl]carbamic acid tert-butyl esterYield 80.1%

Procedure

Same procedure as EXAMPLE 101D, but using (2-oxopyrrolidin-3-(R)-yl)carbamic acid tert-butyl ester (312 mg, 1.56 mmol) and 7-bromomethyl-1-chloroisoquinoline (440 mg, 1.72 mmol) as the starting materials. The crude product is purified by column chromatography on silica with 50-100% ethyl acetate/hexanes. The product fractions are combined and concentrated to give the product as a pale yellow powder (471 mg. 1.25 mmol).

Workup

  1. customThe crude product is purified by column chromatography on silica with 50-100% ethyl acetate/hexanes
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6ad96b33444c4a4a98c1fe0d27392390
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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