Carbon tetrabromide → tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate

HRID 1864008Notes

Reaction equation

HRID 1864008 reaction equation
O[CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 24730280tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(hydroxymethyl)-1-pyrrolidinecarboxylate (0.56 g, 2.8 mmol) with carbon tetrabromide (1.39 g, 4.2 mmol) in methylene chloride (10 mL) was added drop wise a solution of triphenyl phosphine (0.73 g, 2.8 mmol in 5 mL of methylene chloride). Upon completion the mixture was stirred 18 h at room temperature. The solvent was removed at reduced pressure and the residue stirred in 10% ethyl acetate 90% hexane. The mixture was filtered and the resulting solution chromatographed on silica eluting with a gradient of 0-25% EtOAc in hexane to afford the desired compound (0.41 g, 55%). MS (ES+) m/z 264 (M+H)+.

Workup

  1. customThe solvent was removed at reduced pressure
  2. stirringthe residue stirred in 10% ethyl acetate 90% hexane
  3. filtrationThe mixture was filtered
  4. customthe resulting solution chromatographed on silica eluting with a gradient of 0-25% EtOAc in hexane

Sources & evidence

ORD record
ord-b8a367e570ef48609b6c5fd4ae918c69
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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