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

HRID 2425772Notes

Reaction equation

HRID 2425772 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 111.7, 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-614b6a5182e94b2d920e92f1b5c8fb21
Source dataset
uspto-grants-2011_06
Patent number
US07964560B2

Reaction notes

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