1-(Diphenylmethyl)azetidin-3-one → 1-Benzhydryl-3-methylazetidin-3-ol

HRID 222322

Reaction equation

[CH3:1][Mg]I.[C:4]1([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]2[CH2:14][C:13](=[O:15])[CH2:12]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(OCC)C>[C:16]1([CH:10]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:11]2[CH2:14][C:13]([CH3:1])([OH:15])[CH2:12]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl magnesium iodide (3M in diethyl ether, 1.4 mL, 4.2 mmol) was added dropwise to an ice-cold solution of 1-(diphenylmethyl)-3-azetidinone (1 g, 4.20 mmol) in diethyl ether (25 mL) and the mixture was stirred for 1 hour at 0° C. The crude reaction mixture was then purified directly by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 95:5, to afford the title compound the title compound as a pale yellow oil in 68% yield, 730 mg. 1H NMR (CDCl3, 400 MHz) δ: 1.54 (s, 3H), 3.02 (m, 2H), 3.22 (m, 2H), 4.39 (s, 1H), 7.20 (m, 4H), 7.26 (m, 4H), 7.41 (m, 2H); LRMS ESI+ m/z 254 [M+H]+

Workup

customThe crude reaction mixture
customwas then purified directly by column chromatography on silica gel
washeluting with dichloromethane

Sources & evidence

ORD record: ord-35d7b925ab3e4019baa5591dbc185372
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207198B2

Linked notes

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