Dimethyl Sulfoxide → (2S)-1-tert-butoxycarbonyl-2-phenylpiperidin-3-one
Reaction equation
CS(C)=O.CN(C)CCCN=C=NCC.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][C@H:25]([OH:29])[C@@H:24]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[C@@H:24]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Alternatively, dimethyl sulfoxide (20.80 mL, 22.90 g, 29.3 mmol) in dichloromethane (75 mL) is added dropwise to a cooled (0° C.) solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (160 mmol) in dichloromethane (350 mL). The mixture is stirred at 0° C. for 15 min., then (2S,3S)-1-tert-butoxycarbonyl-3-hydroxy-2-phenylpiperidine (36.91 g. 133 mmol) in dichloromethane (150 mL) is added dropwise. The mixture was stirred at 0° C. for 20 min and pyridine (400 mmol) is added slowly followed by trifluroacetic acid (400 mmol). The mixture is allowed to warm to 0° C. and diluted with ice-cooled dichloromethane (250 mL). The mixture is washed with ice cold aqueous citric acid solution (5%, 2×300 mL) and water (300 mL), dried (MgSO4), and the solvent is evaporated under reduced pressure to give (2S)-1-tert-butoxycarbonyl-2-phenylpiperidi n-3-one.
Workup
- stirringThe mixture was stirred at 0° C. for 20 min
- temperatureto warm to 0° C.
- additiondiluted with ice-
- washThe mixture is washed with ice cold aqueous citric acid solution (5%, 2×300 mL) and water (300 mL)
- dry with materialdried (MgSO4)
- customthe solvent is evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-3678cfd6da4a49b2ad3ce75028536fec
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388083B2
Reaction notes
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