Carbon tetrabromide → (4S)-4-(2-Bromoethyl)-4-methoxymethyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

HRID 1917322Notes

Reaction equation

HRID 1917322 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.OC[CH2:27][C@:28]1([CH2:42][O:43][CH3:44])[CH2:32][N:31]([C@@H:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:34])[C:30](=[O:41])[CH2:29]1>ClCCl>[Br:5][CH2:1][CH2:27][C@:28]1([CH2:42][O:43][CH3:44])[CH2:32][N:31]([C@@H:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:34])[C:30](=[O:41])[CH2:29]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67491006(4R)-4-(2-Hydroxyethyl)-4-methoxymethyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

Product 1

HCID 67490858(4S)-4-(2-Bromoethyl)-4-methoxymethyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-oneYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (3.58 g, 10.8 mmol) and triphenylphosphine (2.83 g, 10.8 mmol) were sequentially added to a solution of (4R)-4-(2-hydroxyethyl)-4-methoxymethyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-one (2.85 g, 10.3 mmol) in dichloromethane (30 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred for 10 minutes. The mixture was heated to room temperature and stirred for 24 hours, and then the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane→hexane:ethyl acetate=2:1→1:1→1:2) to give 2.07 g (59%) of the title compound as a colorless oil.

Workup

  1. stirringstirred for 24 hours
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (dichloromethane→hexane:ethyl acetate=2:1→1:1→1:2)

Sources & evidence

ORD record
ord-609b2a52a885484788542d09957a4d7a
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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