Reacción #1993

ord-d35336a8d63f46faa12cbe3c8194e4f3

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe reaction mixture was washed with NaHCO3 solution and water
  2. 2
    Otrothe solvent was removed
  3. 3
    OtroThe residue was chromatographed on silica gel

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726182uspto-grants-1998_03