Potassium tert-butoxide → 1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid
Reaction equation
CC(C)([O-])C.[K+].[N:7]1([C:13]([N:15]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH2:18][CH:17]([C:32]([O:34]C)=[O:33])[CH2:16]2)=[O:14])[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1>CO>[N:7]1([C:13]([N:15]2[CH2:20][CH:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=3)[CH2:18][CH:17]([C:32]([OH:34])=[O:33])[CH2:16]2)=[O:14])[CH2:8][CH2:9][S:10][CH2:11][CH2:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
20.4 g (182 mmol) of potassium tert-butoxide were added at RT to a solution of 7.85 g (18.2 mmol) of the compound from Example 24A in methanol (650 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. The reaction led to an 85:15 cis/trans isomer mixture. Yield: 7.70 g (99% of theory)
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-ad6c87d2eafb417ca7d42539e94361fa
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440657B2
Reaction notes
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