Potassium tert-butoxide → 1-Acetyl-5-[4-(2,2-difluoroethyl)phenyl]piperidine-3-carboxylic acid

HRID 220048Notes

Reaction equation

CC(C)([O-])C.[K+].[C:7]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([F:25])[F:24])=[CH:18][CH:17]=2)[CH2:13][CH:12]([C:26]([O:28]C)=[O:27])[CH2:11]1)(=[O:9])[CH3:8]>CO>[C:7]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([F:24])[F:25])=[CH:18][CH:17]=2)[CH2:13][CH:12]([C:26]([OH:28])=[O:27])[CH2:11]1)(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

410 mg (3.65 mmol) of potassium tert-butoxide were added at RT to a solution of 205 mg (0.365 mmol, purity 61%) of the compound from Example 58A in methanol (6.9 ml). The mixture was stirred at 60° C. overnight. For workup, the methanol was removed under reduced pressure, the residue was admixed with water and the mixture was acidified (pH 1) with aqueous 1 N hydrochloric acid solution. The mixture was extracted with ethyl acetate, and the organic phase was dried with magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 153 mg (67% of theory, purity 50%)

Workup

customFor workup, the methanol was removed under reduced pressure
extractionThe mixture was extracted with ethyl acetate
dry with materialthe organic phase was dried with magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f02235104ddc49259f89ec76b46f8cb5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202862B2

Reaction notes

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