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

HRID 1917315Notes

Reaction equation

HRID 1917315 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([O:32][CH2:33][C@@:34]1([CH2:48]CO)[CH2:38][N:37]([C@@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:40])[C:36](=[O:47])[CH2:35]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH2:25]([O:32][CH2:33][C@@:34]1([CH2:48][CH2:1][Br:5])[CH2:38][N:37]([C@@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:40])[C:36](=[O:47])[CH2:35]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67490855(4R)-4-Benzyloxymethyl-4-(2-hydroxyethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

Product 1

HCID 67491044(4S)-4-Benzyloxymethyl-4-(2-bromoethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (3.17 g, 9.56 mmol) and triphenylphosphine (2.51 g, 9.56 mmol) were sequentially added to a solution of (4R)-4-benzyloxymethyl-4-(2-hydroxyethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one (3.22 g, 9.10 mmol) in dichloromethane (20 mL) in a nitrogen atmosphere, and the mixture was stirred for 15 minutes. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→1:2) to give 3.18 g (84%) of the title compound as a pale yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→1:2)

Sources & evidence

ORD record
ord-c0e837840ea349398ef48c767e69f3a0
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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