Carbon tetrabromide → HCID 67491103, compound

HRID 1917406Notes

Reaction equation

HRID 1917406 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([CH2:46][C:47](=C)[CH2:48]O)[CH2:36][C:35](=[O:37])[N:34]([C@@H:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH3:39])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30]([C@@:32]1([CH2:46][C:47](=[CH2:48])[CH2:1][Br:5])[CH2:36][C:35](=[O:37])[N:34]([C@@H:38]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH3:39])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67490972(3S)-3-(3-Hydroxy-2-methylene-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67491103HCID 67491103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (3.24 g, 9.77 mmol) and triphenylphosphine (2.57 g, 9.80 mmol) were added to a solution of (3S)-3-(3-hydroxy-2-methylene-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester in dichloromethane (113 ml) under ice water-cooling in a nitrogen atmosphere. The mixture was stirred under ice water-cooling for 15 minutes and then concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→80:20→75:25→66:34) to give 3.22 g of the title compound as white crystals.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. temperaturecooling for 15 minutes
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→80:20→75:25→66:34)

Sources & evidence

ORD record
ord-04e3927b98444ae2a6799a90a37df101
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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