Carbon tetrabromide → (3S)-3-(2-Bromoethyl)-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([O:29][C:30]([C@@:32]1([CH2:47]CO)[CH:36]([CH3:37])[C:35](=[O:38])[N:34]([C@@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:40])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30]([C@@:32]1([CH2:47][CH2:1][Br:5])[CH:36]([CH3:37])[C:35](=[O:38])[N:34]([C@@H:39]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH3:40])[CH2:33]1)=[O:31])([CH3:26])([CH3:27])[CH3:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Carbon tetrabromide (1.64 g, 4.95 mmol) and triphenylphosphine (1.30 g, 4.95 mmol) were sequentially added to a solution of (3S)-3-(2-hydroxyethyl)-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (1.56 g, 4.50 mmol) in dichloromethane (20 mL) in a nitrogen atmosphere at 0° C. After heating to room temperature, the reaction solution was stirred for 10 minutes and concentrated to about 5 mL. The residue was purified by silica gel column chromatography (dichloromethane→hexane:ethyl acetate=4:1→2:1→1.5:1) to give 1.30 g (70%) of the diastereomer mixture title compound as a white solid.
Workup
- concentrationconcentrated to about 5 mL
- customThe residue was purified by silica gel column chromatography (dichloromethane→hexane:ethyl acetate=4:1→2:1→1.5:1)
Sources & evidence
- ORD record
- ord-ee04842e138b431cb727a2b4fd0b403c
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618094B2
Reaction notes
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