Reaction #1993

ord-d35336a8d63f46faa12cbe3c8194e4f3

Reaction equation

CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]
alcohol
CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]
3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanol
CS(=O)(=O)Cl
methanesulfonyl chloride
→
CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCOS(C)(=O)=O)C[N+](=O)[O-]
title compound
CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCOS(C)(=O)=O)C[N+](=O)[O-]
3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanyl methylsulfonyl ether

Reactants

CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]
alcohol
CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]
3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanol
—
TEA
CS(=O)(=O)Cl
methanesulfonyl chloride

Reagents

None

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashThe reaction mixture was washed with NaHCO3 solution and water
  2. 2
    Otherthe solvent was removed
  3. 3
    OtherThe residue was chromatographed on silica gel

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726182uspto-grants-1998_03