Potassium tert-butoxide → 1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

HRID 220017Notes

Reaction equation

HRID 220017 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:25]([O:27]C)=[O:26])[CH2:10]2)=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>>[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:25]([OH:27])=[O:26])[CH2:10]2)=[O:8])[CH2:2][CH2:3][S:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58116492Methyl 1-(thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylate

Product 1

HCID 581165611-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Procedure

According to General Method 5A, 5.16 g (12.4 mmol) of the compound from Example 15A and 13.9 g (124 mmol) of potassium tert-butoxide were reacted. The reaction led selectively to the cis isomer. Yield: 4.90 g (98% of theory)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c3b76588eb1f4e8da610d2d4d58223d7
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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