Trifluoroacetic acid → 3-Piperidin-4-yl-7-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1986941

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2(O)[CH:18]([C:19]([O:21][CH3:22])=[O:20])[S:17][C:16]3[C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=[CH:26][C:15]2=3)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:22][O:21][C:19]([C:18]1[S:17][C:16]2[C:23]([C:27]([F:29])([F:30])[F:28])=[CH:24][CH:25]=[CH:26][C:15]=2[C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:20]

Participants

Conditions

Temperature: 40 °C

Procedure

To a room temperature solution of 4-(3-hydroxy-2-methoxycarbonyl-7-trifluoromethyl-2,3-dihydro-benzo[b]thiophen-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (6.00 g, 13.0 mmol) in DCM (30 mL) was added TFA (30 mL) causing-rapid gas evolution. After 5 min, the reaction was stirred at 40° C. for 5.5 h. After cooling to room temperature, the reaction was poured into 20% aqueous potassium carbonate (400 mL) and extracted with DCM (2×200 mL). The combined extracts were dried over magnesium sulfate, filtered, and the solvent removed to give a thick oil. After drying under high vacuum 4.37 g (98%) of the desired product was obtained as a white foam.

Workup

temperatureAfter cooling to room temperature
extractionextracted with DCM (2×200 mL)
dry with materialThe combined extracts were dried over magnesium sulfate
filtrationfiltered
customthe solvent removed
customto give a thick oil
dry with materialAfter drying under high vacuum 4.37 g (98%) of the desired product
customwas obtained as a white foam

Sources & evidence

ORD record: ord-d5b390cb419b45d6a61e2b9210a28b28
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550469B2

Linked notes

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