1-Methoxymethylcyclopropylsulfonylamine tert-butylcarbamate → 1-(Methoxymethyl)cyclopropane-1-sulfonamide

HRID 2358333Notes

Reaction equation

HRID 2358333 reaction equation
C(NC(=O)O)(C)(C)C.[CH3:9][O:10][CH2:11][C:12]1([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:14][CH2:13]1>C(O)(C(F)(F)F)=O.ClCCl>[CH3:9][O:10][CH2:11][C:12]1([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:14][CH2:13]1

Participants

3

Reactant 1

HCID 667523821-Methoxymethylcyclopropylsulfonylamine tert-butylcarbamate

Product 1

HCID 224992771-(Methoxymethyl)cyclopropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

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 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).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed over 80 g of SiO2 (
  3. washeluting 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)

Sources & evidence

ORD record
ord-27c995066e8641c1a4c77a90e3894fd2
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

Loading…