Reaction #632008

ord-6d20e2ce2296407ca15246884a172a42

Reaction equation

CCOC(C)=O
ethyl acetate
CC(C)(C)NS(=O)(=O)C1(C)CC1
N-tert-butyl-(1-methyl)cyclopropylsulfonamide
BrCc1ccccc1
benzyl bromide
→
CC(C)(C)NS(=O)(=O)C1(Cc2ccccc2)CC1
desired product
Yield 60.0%
CC(C)(C)NS(=O)(=O)C1(Cc2ccccc2)CC1
N-tert-butyl-(1-benzyl)cyclopropyl-sulfonamide
Yield 60.0%

Reactants

CCOC(C)=O
ethyl acetate
CC(C)(C)NS(=O)(=O)C1(C)CC1
N-tert-butyl-(1-methyl)cyclopropylsulfonamide
BrCc1ccccc1
benzyl bromide

Reagents

None

Solvents

CCCCCC
hexane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThis compound was obtained in 60% yield

Procedure

This compound was obtained in 60% yield using the procedure described for the synthesis of N-tert-butyl-(1-methyl)cyclopropylsulfonamide using 1.05 equivalents of benzyl bromide. Trituration with 10% ethyl acetate in hexane provided the desired product: 1H NMR (CDCl3) δ 0.92 (m, 2H), 1.36 (m, 2H), 1.43 (s, 9H), 3.25 (s, 2H), 4.62 (br s, 1H), 7.29-7.36 (m, 5H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07935670B2uspto-grants-2011_05