N-tert-butyl-3-chloropropane-1-sulfonamide → N-tert-Butylcyclopropanesulfonamide
Reaction equation
[Li]CCCC.[C:6]([NH:10][S:11]([CH2:14][CH2:15][CH2:16]Cl)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7]>C1COCC1>[C:6]([NH:10][S:11]([CH:14]1[CH2:16][CH2:15]1)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-BuLi (86.7 mL, 138.8 mmol, 1.6 M in hexane) was dissolved in dry THF (120 mL) and cooled to −78° C. under a argon atmosphere. To this solution was added a solution of N-tert-butyl-(3-chloro)propylsulfonamide from Step B.2 (14.5 g, 67.8 mmol) in dry THF (160 mL) slowly dropwise over 60 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 CH2Cl2 (100 mL) and water (100 mL). The organic phase was washed with aqueous 1N NaOH (150 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the N-tert-Butyl cyclopropylsulfonamide as a waxy off white solid (12 g, 100%): 1H NMR (CDCl3) δ 0.98 (m, 2H), 1.17 (m, 2H), 1.38 (s, 9H), 2.45 (m, 1H), 4.45 (br s, 1H). 13C NMR (CDCl3) δ 6.5, 30.6, 33.5, 54.2. MS (ESI) 176 (M+−H).
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 CH2Cl2 (100 mL) and water (100 mL)
- washThe organic phase was washed with aqueous 1N NaOH (150 mL), brine (100 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-db15d7286cea454db753be52d1a2bd6d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601686B2
Reaction notes
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