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

HRID 499076Notes

Reaction equation

[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.O.C(OCC)(=O)C>CS(C)=O>[CH:7]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred slurry of 1-(diphenylmethyl)-3-hydroxyazetidine (30 g, 0.126 mol) in triethylamine (63 g, 0.628 mol) was added a solution of sulfur trioxide pyridine complex (60 g, 0.376 mol) in anhydrous DMSO (300 ml) dropwise over 30 minutes. The resulting mixture was warmed to 50° C. for 30 minutes. The reaction mixture was then cooled to ambient and poured into a mixture of water (1L) and ethyl acetate (800 ml). The organic layer was separated and the aqueous layer extracted with ethyl acetate (3×200 ml). The combined organic solutions were then washed with water (3×200 ml), then saturated brine (200 ml), dried (magnesium sulfate), filtered and concentrated. The residue was purified on silica gel, eluting with 5-10% ethyl acetate/petrol. The product was obtained as a white solid (26.2 g, 86%); 1H NMR CDCl3 δ 4.07 (4H, s), 4.62 (1H, s), 7.20-7.39 (6H, m), 7.53 (4H, d).

Workup

temperatureThe reaction mixture was then cooled to ambient and
customThe organic layer was separated
extractionthe aqueous layer extracted with ethyl acetate (3×200 ml)
washThe combined organic solutions were then washed with water (3×200 ml)
dry with materialsaturated brine (200 ml), dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel
washeluting with 5-10% ethyl acetate/petrol

Sources & evidence

ORD record: ord-19740f51e390435bba57eef2d65a6f14
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767672B2

Reaction notes

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