Carbon tetrabromide → tert-Butyl 2-(2,2-dibromoethenyl)pyrrolidine-1-carboxylate

HRID 653845Notes

Reaction equation

HRID 653845 reaction equation
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34](Br)(Br)([Br:36])[Br:35]>C(Cl)Cl>[Br:35][C:34]([Br:36])=[CH:1][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 14730280tert-Butyl 2-(2,2-dibromoethenyl)pyrrolidine-1-carboxylateYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following the procedure of Example 3, 6.8 g of (S)-2-formyl-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester in 20 ml of methylene chloride is reacted with 40 g of triphenylphosphine, 26 g of carbon tetrabromide in 700 ml of methylene chloride to give 5.8 g of the desired product as a colorless solid, mp 58°-59° C., [α]D26° =+24°±1 (C=1.048%, methylene chloride).

Sources & evidence

ORD record
ord-87285bdd070d4b0ca5caf749ab7a2944
Source dataset
uspto-grants-1992_07
Patent number
US05128483

Reaction notes

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