Acetone → HCID 57182831, compound

HRID 2254392Notes

Reaction equation

[CH3:1][C:2]1(C)O[O:3]1.C=C.[C:8]1([CH:14]2[CH2:19][C:18](=[O:20])[CH2:17][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)=[O:29]>>[CH2:2]1[O:3][C:18]2([CH2:19][CH:14]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:15]([OH:29])[CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:17]2)[O:20][CH2:1]1

Participants

Reactant 3

HCID 180Acetone2×

HCID 115197Dimethyldioxirane

HCID 19745020HCID 19745020, compound

Product 1

HCID 57182831HCID 57182831, compoundYield 72%

Conditions

Temperature: 0 °C

Procedure

812 mL (40.6 mmol) of dimethyldioxirane, 0.050M in acetone, is added via a cannula to a 0° C. solution of 12.0 g (40.6 mmol) of 2,6-diphenyl-4-piperidone ethylene petal in 100 mL acetone. After stirring for ten minutes at 0° C., the reaction mixture is concentrated under reduced pressure and the residue is recrystallized from methanol to yield 9.0 g (72%) of the title compound as a white solid, melting at 161°-162° C.

Workup

concentrationthe reaction mixture is concentrated under reduced pressure
customthe residue is recrystallized from methanol

Sources & evidence

ORD record: ord-bd149333159e43ee8a089f74e29e59fc
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05235056

Reaction notes

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