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

HRID 922558Notes

Reaction equation

HRID 922558 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

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

Product 1

HCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3.44 g (187 mmol) (S)-1-Boc-3-pyrrolidinol in 15 ml THF are added 1.70 mL (21.6 mmol) of methanesulfonyl chloride at 0° C. The reaction mixture is stirred for 1 h. Water is added and it is extracted with EtOAc (3×). The organic layer is washed with an aq. NaHCO3 solution and dried over MgSO4. The solvent is removed in vacuo.

Workup

  1. extractionit is extracted with EtOAc (3×)
  2. washThe organic layer is washed with an aq. NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0a090a72c35e45f3a1fae04bdafe52a4
Source dataset
uspto-grants-2016_03
Patent number
US09278954B2

Reaction notes

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