Triethylamine → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 516139Notes

Reaction equation

HRID 516139 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(OCC)(=O)C>C(Cl)(Cl)Cl.O>[CH3:21][S:22]([O:13][CH: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)(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

N-Boc-3-pyrrolidinol (1000 mg) was dissolved in chloroform (20 ml). Triethylamine (1.15 ml) and methanesulfonyl chloride (498 μl) were added thereto at 0° C. After stirring at room temperature for 1.0 hour, ethyl acetate and water were added thereto to separate the organic layer. After being washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution and water, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a colorless, oily compound (1.2 g). Physical properties: m/z [M+H]+ 266.1

Workup

  1. customat 0° C
  2. customto separate the organic layer
  3. washAfter being washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated aqueous ammonium chloride solution and water, the organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-705913ace0f9428e984fc2a96196d474
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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