Water → 1-(Diphenylmethyl)azetidine-3-carbonitrile

HRID 2066269Notes

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.O.[C-:24]#[N:25].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH:1]([N:14]1[CH2:17][CH:16]([C:24]#[N:25])[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: 65 °C

Procedure

To a solution of 1-benzhydryl-3-(methanesulfonyloxy)azetidine (7.52 g) in N,N-dimethylformamide (60 ml) were added water (7.2 ml) and sodium cyanide (3.48 g), followed by stirring at 65° C. for 9 hr. To the reaction mixture were added water, sodium carbonate and ethyl acetate, and this was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layer was combined, washed with brine, and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resultant crystals were suspended by addition of diethyl ether (10 ml). The crystals were collected by filtration and washed with diethyl ether. This was dried under aeration to provide the titled compound as pale yellow crystals (5.43 g, 92.3%).

Workup

customthis was partitioned
extractionThe aqueous layer was extracted with ethyl acetate
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationThis was concentrated under reduced pressure
additionthe resultant crystals were suspended by addition of diethyl ether (10 ml)
filtrationThe crystals were collected by filtration
washwashed with diethyl ether
customThis was dried under aeration

Sources & evidence

ORD record: ord-1f7229d0f2df4196a1483c123b4a39e7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288538B2

Reaction notes

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