Carbon tetrabromide → tert-Butyl (3S)-3-bromopyrrolidine-1-carboxylate

HRID 2196539Notes

Reaction equation

HRID 2196539 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C@H:10]1[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 34179480tert-Butyl (3S)-3-bromopyrrolidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-Boc-(R)-3-hydroxypyrrolidine (0.936 g, 5 mmol) in THF (25 mL) was added carbon tetrabromide (2.487 g, 7.50 mmol) followed by triphenylphosphine (1.967 g, 7.50 mmol). The resulting suspension was allowed to stir at 60° C. for 1 h. Insoluble material was filtered, and concentrated. The residue was purified by silica gel column chromatography with a gradient of EtOAc (5-30%) in hexanes to afford 72 (1.12 g, 90%) as a colorless oil. LRMS (ESI): calc. 249.0; found 271.9 (MNa)+.

Workup

  1. filtrationInsoluble material was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography with a gradient of EtOAc (5-30%) in hexanes

Sources & evidence

ORD record
ord-0952324dd17847ae938a80f3c0f9a69e
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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