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

HRID 370004Notes

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.N1C=CC=CC=1.S(=O)(=O)=O>CS(C)=O>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][C:10](=[O:12])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of 1-diphenylmethyl-3-hydroxyazetidine (3.3 g, 14 mmol; J. Org. Chem. 1972, 37, 3953) in dimethyl sulphoxide (20 ml) was treated with triethylamine (19.2 ml), cooled to 15° C. and treated with sulphur trioxide pyridine (13.8 g) in dimethyl sulphoxide (30 ml), keeping the temperature below 20° C. The solution was stirred under an atmosphere of nitrogen at 15° C. for 45 minutes then at room temperature for 45 minutes. The solution was poured into ice water and extracted twice with ethyl acetate. The organic layer was collected, washed twice with water, dried (sodium sulphate), evaporated to dryness and the crude product purified using a plug of silica by eluting with dichloromethane to afford the ketone as a gum (2.9 g, 89%), δ (360 MHz, CDCl3) 4.00 (4H, s), 4.59 (1H, s), 7.12-7.49 (10H, m).

Workup

customthe temperature below 20° C
waitat room temperature for 45 minutes
extractionextracted twice with ethyl acetate
customThe organic layer was collected
washwashed twice with water
dry with materialdried (sodium sulphate)
customevaporated to dryness
customthe crude product purified
washby eluting with dichloromethane

Sources & evidence

ORD record: ord-d58a6f151f09443a8129a633eb117396
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140347

Reaction notes

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