Reaction #632013

Reaction equation

1-methoxymethylcyclopropylsulfonylamine tert-butylcarbamate

→

desired product

1-methoxymethylcyclopropysulfonamide

Solvents

TFA dichloromethane

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   Otherthe residue purified by column chromatography over 80 g of SiO2 (eluting with 0% to 60% ethyl acetate/hexanes)

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 purified by column chromatography over 80 g of SiO2 (eluting with 0% to 60% ethyl acetate/hexanes) to provide the desired product 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).

Source