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

HRID 1045685Notes

Reaction equation

HRID 1045685 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>O1CCCC1>[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 111.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (11 g, 57 mmol) and triethylamine (17.3 g, 171 mmol) in tetrahydrofuran (180 ml) was added methanesulfonyl chloride (9.8 g, 85.5 mmol) at 5° C. The mixture was stirred for 3 hours at room temperature, poured into water, and extracted with ethyl acetate. The organic extract was washed with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford (S)-3-methanesulfonyloxypyrrolidine-1-carboxylic acid tert-butyl ester (16.9 g, quant.) as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8ac44d697f443fca71f3fab04d80d21
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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