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

HRID 85114Notes

Reaction equation

HRID 85114 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].CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of N-Boc-3-hydroxypyrrolidine (28; 2 g, 10.7 mmol) and Et3N (2.2 ml, 16.0 mmol) in CH2Cl2 (5 mL) was added a solution of methanesulfonyl chloride (1.84 g, 2.52 ml, 16.0 mmol) in CH2Cl2 (5 mL) dropwise in an ice-water bath. The mixture was stirred at room temperature for 18 h. It was then diluted with 50 mL of CH2Cl2, washed with saturated Na2CO3 (20 mL), brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to afford N-Boc-3-(methylsulfonyloxy)pyrrolidine 29 (2.6 g, 92%). This material was used in the following step without further purification.

Workup

  1. washwashed with saturated Na2CO3 (20 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9118f313eb5344b7a62d2245e06e9311
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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