1-(Diphenylmethyl)azetidin-3-ol → 1-(Diphenylmethyl)azetidin-3-one
Reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(N(CC)CC)C.CS(C)=O.O>[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
The title compound was prepared as described in WO2010079443A1. To a solution of compound 1-benzhydrylazetidin-3-ol (20 g, 28.4 mmol) in the triethyl amine (60 mL) was added a solution of sulfur trioxide pyridine complex (SO3.Py) (40 g, 251.6 mmol) in dimethylsulfoxide (260 mL) under a nitrogen atmosphere at 25° C. The reaction was stirred at 50° C. for 2 h. Then the reaction mixture was cooled back to 25° C., diluted with water (500 mL), and extracted with ethyl acetate (2×500 mL). Organic part was dried over sodium sulfate, filtered, and concentrated under a vacuum to give a crude compound which was further purified by column chromatography using silica gel (100 to 200 mesh) eluting with 0% to 20% ethyl acetate in hexanes to provide 1-benzhydrylazetidin-3-one (11.7 g) as a white solid. MS (ESI, positive ion) m/z (M+1): 238.30. 1H NMR (400 MHz, DMSO) δ 7.50 (d, J=7.5 Hz, 4H), 7.30 (t, J=7.5 Hz, 4H), 7.20 (t, J=7.3 Hz, 2H), 4.82 (s, 1H), 4.00 (s, 4H).
Workup
- temperatureThen the reaction mixture was cooled back to 25° C.
- extractionextracted with ethyl acetate (2×500 mL)
- dry with materialOrganic part was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under a vacuum
- customto give a crude compound which
Sources & evidence
- ORD record
- ord-91d1743e54494d7ea727238ee7bb9c4d
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
Loading…