Carbon tetrabromide → HCID 67491102, compound

HRID 1917418Notes

Reaction equation

HRID 1917418 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[C@H:12]([C:13]([CH2:15]O)=[CH2:14])[CH2:11][N:10]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47]>ClCCl>[C:1]([O:5][C:6]([C@H:8]1[C@H:12]([C:13]([CH2:15][Br:47])=[CH2:14])[CH2:11][N:10]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67490895HCID 67490895, compound

Product 1

HCID 67491102HCID 67491102, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,4R)-1-Benzyloxycarbonyl-4-[1-(hydroxymethyl)vinyl]pyrrolidine-3-carboxylic acid tert-butyl ester (30.0 g, 83.0 mmol) was dissolved in dichloromethane (300 mL). Triphenylphosphine (23.2 g, 87.2 mmol) and carbon tetrabromide (29.4 g, 87.2 mmol) were added, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure. Then, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→1:1) to give 26.9 g of the title compound as a colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThen, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→1:1)

Sources & evidence

ORD record
ord-39e927de30484c0392b61b1bb4b0de03
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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