Hydrochloric Acid → 1-(Diphenylmethyl)azetidine-3-carboxylic acid

HRID 2265700Notes

Reaction equation

[CH:1]([N:14]1[CH2:17]C(C#N)[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.[OH-].[K+].Cl.[Cl-].[Na+].C[O:26][CH:27]([OH:29])[CH3:28]>O>[CH:1]([N:14]1[CH2:17][CH:28]([C:27]([OH:29])=[O:26])[CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-benzhydryl-3-cyanoazetidine (5.43 g) in methoxyethanol (54 ml) were added potassium hydroxide (6.48 g) and water (3.25 ml), followed by stirring at 100° C. for 4 hr. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was poured into ice. After adjusting this to pH 5 with 1N hydrochloric acid, sodium chloride was added thereto. This was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer after drying was concentrated under reduced pressure to provide a crude product of the titled compound as pale yellow crystals. The crystals were suspended by addition of diethyl ether (15 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 (4.20 g, 71.7%).

Workup

temperatureto cool down to room temperature
additionThe reaction mixture was poured into ice
additionwas added
extractionThis was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe organic layer after drying
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-c0bafda231534bf587710ebce7035e6f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855290B2

Reaction notes

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