Triethylamine → tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

HRID 494883

Reaction equation

HRID 494883 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:11][CH2:10][C@@H:9]1[CH2:12][CH2:13][CH2:14][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 10039261tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylateYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc-(2S)-prolinol (6.04 g) in 100 mL of dichloromethane was treated with 4.04 g of triethylamine, cooled to 0° C., and treated with methanesulfonyl chloride (4.0 g) slowly. After stirring at 0° C. for 30 minutes, the reaction was allowed to warm to room temperature, washed with 5% aqueous NaHCO3 solution, dried over sodium sulfate, and concentrated to dryness to give the title compound as an off-white oil (8.47 g).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with 5% aqueous NaHCO3 solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-833a994639cd4f4f8d723756e456ed88
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Linked notes

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