Water → cis-3-hydroxy-4-phenylazetidin-2-one

HRID 1742082Notes

Reaction equation

[OH-].[K+].C([O:6][C@H:7]1[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][C:8]1=[O:17])(=O)C.O.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:6][C@H:7]1[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][C:8]1=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 200 mL of THF and 280 mL of 1M aqueous potassium hydroxide solution at 0° C. was added a solution of 4.59 g (22.4 mmol) of cis-3-acetoxy-4-phenylazetidin-2-one in 265 mL of THF via a dropping funnel over a 40 rain period. The solution was stirred at 0° C. for 1 h and 100 mL of water and 100 mL of saturated sodium bicarbonate were added. The mixture was extracted with four 200 mL portions of ethyl acetate and the combined organic layers were dried over sodium sulfate and concentrated to give 3.54 g (97%) of racemic cis-3-hydroxy-4-phenylazetidin-2-one as white crystals, m.p. 147°-149° C. this material was resolved into its enantiomers by recrystallization of its 2-methoxy-2-(trifluoromethyl)phenylacetic ester from hexane acetone followed by hydrolysis [α]25Hg177°.

Workup

extractionThe mixture was extracted with four 200 mL portions of ethyl acetate
dry with materialthe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-adb36a4300614e4a8dc13f09125bdb56
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05336785

Reaction notes

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