1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 2-[1-(diphenylmethyl)azetidin-3-yl]-1H-isoindole-1,3(2H)-dione

HRID 620923Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[CH:1]([N:14]1[CH2:17][CH:16]([N:27]2[C:26](=[O:28])[C:25]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]3[C:23]2=[O:33])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 0.362 mol of 1-benzhydryl-3-mesyloxyazetidine (J. Org. chem. 1972, 37, 3953-3955), 0.44 mol of potassium phthalimide and 0.045 mol of hexadecyltributylphosphonium bromide in 500 ml of anhydrous toluene is heated at reflux for 5 hours, then it is cooled at 20° C. The precipitate is filtered, washed with 400 ml of ethyl acetate and discarded. The organic solution is washed with water, dried on anhydrous sodium sulfate, filtered on charcoal and concentrated under reduced pressure. The oily residue is crystallized from 600 ml of diisopropyl ether. Thus, 80 g (Yield: 67.4% of the theoretic) of 1-benzhydryl-3-phthalimidoazetidine are obtained; m.p. 118°-120° C.

Workup

temperatureis heated
temperatureat reflux for 5 hours
filtrationThe precipitate is filtered
washwashed with 400 ml of ethyl acetate
washThe organic solution is washed with water
dry with materialdried on anhydrous sodium sulfate
filtrationfiltered on charcoal
concentrationconcentrated under reduced pressure
customThe oily residue is crystallized from 600 ml of diisopropyl ether

Sources & evidence

ORD record: ord-0ca7d9576e1d45ddafb7dcdf462da0c7
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822895

Reaction notes

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