(6R, 7R)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (3R, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one

HRID 235757Notes

Reaction equation

CC1(C)[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:15])[C@H:5]2[C:10]([O:13][CH3:14])([CH3:12])[CH3:11]>C(O)(=O)C.O>[OH:9][CH2:8][CH2:7][C@H:6]1[NH:3][C:4](=[O:15])[C@H:5]1[C:10]([O:13][CH3:14])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of (6R, 7R)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicylco[4.2.0]octan-8-one (345 mg) in a mixture of acetic acid (5.52 ml) and water (1.38 ml) was heated at 65° C. for 30 minutes. The mixture was cooled to ambient temperature and evaporated in vacuo. Xylene was added to the residue and the resultant suspension was evaporated in vacuo. The crystalline residue was dissolved in a mixture of methanol and xylene and the resultant solution was evaporated in vacuo. This operation was repeated once, and the crystalline residue was washed with hexane to give (3R, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (275 mg).

Workup

temperatureThe mixture was cooled to ambient temperature
customevaporated in vacuo
additionXylene was added to the residue
customthe resultant suspension was evaporated in vacuo
dissolutionThe crystalline residue was dissolved in a mixture of methanol and xylene
customthe resultant solution was evaporated in vacuo
washthe crystalline residue was washed with hexane

Sources & evidence

ORD record: ord-f1c0e507b24c47fe9bf9571f665924cc
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640915

Reaction notes

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