Dimethyl Sulfoxide → 239073-93-9
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]([O:26][CH3:27])([CH2:24][OH:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][C:21]([O:26][CH3:27])([CH:24]=[O:25])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Conditions
- Temperature
- -65 °C
Procedure
To a solution of oxalyl chloride (4.36 ml) in dichloromethane (220 ml) was added dropwise at −70% a solution of dimethylsulfoxide (5.32 ml) in dichloromethane (20 ml), and 30 minutes later, to the mixture was added dropwise a solution of 1-(tert-butoxycarbonyl)-4-methoxy-4-piperidinemethanol (6.13 g) in dichloromethane (60 ml). The mixture was stirred around −65° C. for 1 hour. To the mixture was added triethylamine (17.4 ml), and the mixture was stirred between the temperature ranging from −60° C. to 0° C. for 2 hours. The reaction solution was washed with water and saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1) to give colorless solid of the title compound (6.32 g).
Workup
- stirringthe mixture was stirred between the temperature
- waitranging from −60° C. to 0° C. for 2 hours
- washThe reaction solution was washed with water and saturated brine
- customdried
- concentrationconcentrated
- customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-e128ec512d4444cc8809229eb1292aed
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680312B2
Reaction notes
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