Carbon tetrabromide → 3-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1260282Notes

Reaction equation

HRID 1260282 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:21]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]1.C(Br)(Br)(Br)[Br:34]>C1COCC1>[Br:34][CH:21]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 426142173-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (727 mg, 2.77 mmol) was added to a stirred solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (173 mg, 0.924 mmol) and carbon tetrabromide (919 mg, 2.77 mmol) in THF (3.00 mL) at 0° C., and the resulting mixture was allowed to warm slowly to rt. After 20 h, the reaction was filtered and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 10%-40% EtOAc/hexanes as eluent) afforded the title compound i-4-a. m/z (ES) 250 (MH)+. 1H NMR (500 MHz, CDCl3): δ 4.49 (m, 1H), 3.81 (m, 2H), 3.63 (m, 1H), 3.53 (m, 1H), 2.33 (m, 1H), 2.26 (m, 1H), 1.49 (s, 9H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 10%-40% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-b2b768af207741298559bc4149d2a53c
Source dataset
uspto-grants-2013_06
Patent number
US08470819B2

Reaction notes

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