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

HRID 1712646Notes

Reaction equation

[OH-].[K+].[CH:3]([N:16]1[CH2:19]C(C#N)[CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[Cl-].[Na+].C[O:26][CH:27]([OH:29])[CH3:28]>O>[CH:3]([N:16]1[CH2:19][CH:28]([C:27]([OH:29])=[O:26])[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium hydroxide (6.48 g) and water (3.25 ml) were added to a solution of 1-benzhydryl-3-cyanoazetidine (5.43 g) in methoxyethanol (54 ml), followed by stirring at 100° C. for 4 hours. The reaction mixture was allowed to cool down to room temperature, and poured into ice. After pH of the mixture was adjusted to 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 dried organic layer was concentrated under reduced pressure to give a crude product of the title compound as pale yellow crystals. The crystals were suspended by the addition of diethyl ether (15 ml). The crystals were collected by filtration and washed with diethyl ether. This was dried under aeration to give the title compound (4.20 g, 71.7%) as pale yellow crystals.

Workup

temperatureto cool down to room temperature
additionpoured 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
concentrationThe dried organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-900ba1f6a127427ab0fad4f9c25a38b9
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790885B2

Reaction notes

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