Water → 1-Diphenylmethyl-3-(N-methyl benzenesulphonamido)azetidine
Reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH:10]([N:24]([CH3:23])[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
6
Procedure
To a solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (WO 96/05193) (1.4 g) in dioxane (25 mL) were added N-methyl benzenesulphonamide (1.2 g) and caesium carbonate (2.6 g). The reaction mixture was heated to reflux for 3 h, then cooled to room temperature. Water (20 mL) was added to the resulting slurry, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organics were washed with brine, dried over magnesium sulphate, filtered and dried in vacuo to yield crude product. Chromatography on silica gel eluting with ethyl acetate:hexanes (2:3 by volume) yielded the title compound as a white foam (1.31 g).
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux for 3 h
- extractionthe mixture was extracted with ethyl acetate (3×25 mL)
- washThe combined organics were washed with brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customdried in vacuo
- customto yield crude product
Sources & evidence
- ORD record
- ord-6102f2a111f243de9734956b68074544
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262046B1
Reaction notes
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