Methanesulfonyl chloride → 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanyl methylsulfonyl ether

HRID 1897

Reaction equation

HRID 1897 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([CH2:17][N+:18]([O-:20])=[O:19])[CH2:14][CH2:15][OH:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:16][CH2:15][CH2:14][C@@H:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:17][N+:18]([O-:20])=[O:19])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 228695313-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanol

Product 1

HCID 867503003-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanyl methylsulfonyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.5 g sample of the alcohol from step 471a above was dissolved in 25 mL of methylene chloride and treated with methanesulfonyl chloride an TEA at 0° C. for 2 hours. The reaction mixture was washed with NaHCO3 solution and water, and the solvent was removed. The residue was chromatographed on silica gel to give 3 g of the title compound.

Workup

  1. washThe reaction mixture was washed with NaHCO3 solution and water
  2. customthe solvent was removed
  3. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d35336a8d63f46faa12cbe3c8194e4f3
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

Loading…