Water → 1-(Diphenylmethyl)azetidin-3-one

HRID 28473

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.S(=O)(=O)=O.N1C=CC=CC=1.O>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]=1

Participants

Conditions

Temperature: 10 °C

Procedure

Triethylamine (11.6 ml, 42 mmol) was added to a solution of 1-benzhydryl-azetidin-3-ol (2.0 g, 4.2 mmol) in dimethylsulfoxide (60 mL) at room temperature. The resulting mixture was cooled to 10° C., then pyridine sulfur trioxide (8.64 g, 33.6 mmol) in dimethylsulfoxide was introduced. The mixture was stirred at 10° C. for 1 hour and then for 2 hours at room temperature. The reaction mixture was poured into water (100 mL) and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude oil was column chromatographed on silica gel (30% ethyl acetate-hexane). The product-containing fractions were concentrated under vacuum to give 1.7 g (86%) of the title compound as a yellow solid, m.p. 52-54° C.

Workup

waitfor 2 hours at room temperature
extractionextracted with methylene chloride (3×100 mL)
washThe organic layer was washed with water (3×150 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customchromatographed on silica gel (30% ethyl acetate-hexane)
concentrationThe product-containing fractions were concentrated under vacuum

Sources & evidence

ORD record: ord-2da6b1058eec4ebaa484fa9f3d32c876
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419986B2

Linked notes

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