Water → (S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

HRID 1095089Notes

Reaction equation

HRID 1095089 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidineYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine (7.7 g, 41 mmol) (Aldrich) in dichloromethane (130 mL) at 0° C. was added triethylamine (10.4 g, 103 mmol), and methanesulfonyl chloride (8 g, 70 mmol, Aldrich). The reaction mixture was stirred at 0° C. for 1 h, then at room temperature for 0.5 h. The mixture was poured into water, extracted with dichloromethane. The organic layer was separated, washed with water, brine, dried over MgSO4, and concentrated to give crude (S)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil (Yield 11 g, 100%).

Workup

  1. waitat room temperature for 0.5 h
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e944e3de615042ecb14e70f62f83ef27
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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