Methyl iodide → N-tert-butyl-1-methylcyclopropane-1-sulfonamide

HRID 1019624Notes

Reaction equation

HRID 1019624 reaction equation
[C:1]([NH:5][S:6]([CH2:9][CH2:10][CH2:11]Cl)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li][CH2:14][CH2:15][CH2:16][CH3:17].CI>>[C:1]([NH:5][S:6]([C:9]1([CH3:14])[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1([S:6]([NH2:5])(=[O:8])=[O:7])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11701296N-tert-butyl-3-chloropropane-1-sulfonamideHCID 178418339Butyllithium

Product 2

HCID 21889792N-tert-butyl-1-methylcyclopropane-1-sulfonamideHCID 218898141-Methylcyclopropane-1-sulfonamide

Procedure

The intermediate 1-methylcyclopropane-1-sulfonamide was prepared based on previously reported method (Synlett 2006, 5, 725-278) (Scheme 2). N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide was synthesized using a one-pot procedure from N-(tert-butyl)-3-chloropropane-1-sulfonamide through n-BuLi promoted intramolecular cyclization, lithiation and alkylation with methyl iodide. The removal of the Boc protecting group with TFA afforded 1-methylcyclopropane-1-sulfonamide.

Workup

  1. customThe intermediate 1-methylcyclopropane-1-sulfonamide was prepared
  2. customThe removal of the Boc protecting group with TFA

Sources & evidence

ORD record
ord-476b6abdec0f46d8a4e8ced23b9548db
Source dataset
uspto-grants-2014_05
Patent number
US08716275B2

Reaction notes

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