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

HRID 873335Notes

Reaction equation

HRID 873335 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

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

Product 1

HCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidineYield 123.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (200 mg, 1.07 mmol) and triethylamine (0.3 mL, 1.07 mmol) in DCM (10 mL) at 0° C. was added methane sulfonylchloride (0.125 mL, 1.07 mmol) dropwise. After stirring for 3 h, the reaction mixture was washed with sat. NaHCO3 solution (aq.). The aqueous layer was extracted with DCM and the combined organics were dried (MgSO4), filtered and concentrated in vacuo to give the title compound (350 mg) as a colourless solid which was used in the next step without further purification.

Workup

  1. washthe reaction mixture was washed with sat. NaHCO3 solution (aq.)
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-640cadd9b27f4fd687508002612dd179
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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