Triethylamine → 1-(Diphenylmethyl)azetidin-3-one
Reaction equation
C(N(CC)CC)C.[CH:8]([N:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CS(C)=O>[CH:8]([N:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
Triethylamine (29.1 mL, 209 mmol) and a solution of sulphur trioxide pyridine complex (21.3 g, 134 mmol) in DMSO (100 mL) were added at 10° C. to a solution of 1-benzhydrylazetidin-3-ol (5.0 g, 20.9 mmol) in DMSO (60 mL). The resulting mixture was stirred at 10° C. for 45 minutes, then at room temperature for 4 hours, subsequently quenched by pouring onto crushed ice (˜200 g) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (400 mL) and brine (400 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (80:20 to 70:30) as eluent. The title product was obtained as a yellowish solid (4.35 g, 88%).
Workup
- waitat room temperature for 4 hours
- customsubsequently quenched
- additionby pouring
- customonto crushed ice (˜200 g)
- extractionextracted with ethyl acetate (3×200 mL)
- washThe combined organic layers were washed with water (400 mL) and brine (400 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-84019a90ca1f4ea6b5a18801631c3100
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051321B2
Reaction notes
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