Reacción #1884969

ord-5c8a03cc2fc64d4d9d11dc8352c35e7e

Ecuación de reacción

CC(C)(C)NC(=O)O.COCC1(S(N)(=O)=O)CC1
1-methoxymethylcyclopropylsulfonylamine tert-butylcarbamate
COCC1(S(N)(=O)=O)CC1
1-methoxymethylcyclopropysulfonamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGstirred at room temperature for 16 hours
  2. 2
    OtroThe solvent was removed in vacuo
  3. 3
    Otrothe residue chromatographed over 80 g of SiO2 (
  4. 4
    Lavadoeluting with 0% to 60% ethyl acetate/hexanes to 1-methoxymethylcyclopropylsulfonamide as a white solid (0.55 g, 77% overall over two steps): 1H NMR (CDCl3) δ 0.95 (m, 2H), 1.44 (m, 2H), 3.36 (s, 3H), 3.65 (s, 2H), 4.85 (s, 2H)

Procedimiento

A solution of 1-methoxymethylcyclopropylsulfonylamine tert-butylcarbamate (1.14 g, 4.30 mmol) was dissolved in a solution of 50% TFA/dichloromethane (30 mL) and was stirred stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue chromatographed over 80 g of SiO2 (eluting with 0% to 60% ethyl acetate/hexanes to 1-methoxymethylcyclopropylsulfonamide as a white solid (0.55 g, 77% overall over two steps): 1H NMR (CDCl3) δ 0.95 (m, 2H), 1.44 (m, 2H), 3.36 (s, 3H), 3.65 (s, 2H), 4.85 (s, 2H); 13C NMR (CDCl3) δ 11.17, 40.87, 59.23, 74.80; LRMS m/z 183 (M++NH4)—

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343477B2uspto-grants-2013_01