3-Chloropropylsulfonylamine tert-butylcarbamate → Cyclopropylsulfonylamine tert-butylcarbamate
Reaction equation
C([Li])CCC.[C:6]([NH:10][C:11](=[O:13])[OH:12])([CH3:9])([CH3:8])[CH3:7].Cl[CH2:15][CH2:16][CH2:17][S:18]([NH2:21])(=[O:20])=[O:19]>C1COCC1>[C:6]([NH:10][C:11](=[O:12])[OH:13])([CH3:9])([CH3:8])[CH3:7].[CH:17]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:15][CH2:16]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-butyllithium (74.7 mL, 119.5 mmol, 1.6M in hexane) was dissolved in dry THF (105 mL) and cooled to −78° C. under an argon atmosphere. To this solution was added a solution of 3-chloropropylsulfonylamine tert-butylcarbamate (14 g, 54.3 mmol) in dry THF (105 mL) dropwise over 20-30 minutes. The dry ice bath was removed and the reaction mixture was allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with glacial acetic acid (3.4 mL), concentrated in vacuo, and partitioned between dichloromethane (100 mL) and water (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the desired product as a waxy off-white solid (12.08 g, 100%): 1H NMR (CDCl3) δ 1.10 (m, 2H), 1.34 (m, 2H), 1.50 (s, 9H), 2.88 (m, 1H), 7.43 (s, 1H). 13C NMR (CDCl3) δ 6.21, 28.00, 31.13, 84.07, 149.82.
Workup
- customThe dry ice bath was removed
- temperatureto warm to room temperature over a period of 2 hours
- customThe reaction mixture was quenched with glacial acetic acid (3.4 mL)
- concentrationconcentrated in vacuo
- custompartitioned between dichloromethane (100 mL) and water (100 mL)
- washThe organic phase was washed with brine (100 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4ab5c96f133f4cb5a0e766c94dbb8ab5
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935670B2
Reaction notes
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