tert-Butyl 4-hydroxy-4-(4-(trifluoromethoxy)phenyl)piperidine-1-carboxylate → Tert-butyl 4-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate

HRID 1043529Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -20 °C

Procedure

4-hydroxy-4-(4-(trifluoromethoxy)phenyl)piperidine-1-formic acid tert-butyl ester (1.85 g, 5 mmol) was dissolved in dry dichloromethane (30 mL), cooled to −20° C., added dropwise triethyl silicane (696 mg, 6 mmol), added slowly until completed, slowly resumed to stir for 15 h at room temperature. After the reaction was finished, added ice water to quench reaction, partitioned, organic phases were washed by saturated saline, followed by sodium sulphate drying, concentration, column chromatography (PE: EA=20:1) to give 0.6 g light yellow gel-like substance, yield: 34%.

Workup

additionadded slowly
customto quench
customreaction
custompartitioned
washorganic phases were washed by saturated saline
concentrationfollowed by sodium sulphate drying, concentration, column chromatography (PE: EA=20:1)
customto give 0.6 g light yellow gel-like substance, yield: 34%

Sources & evidence

ORD record: ord-88a02c05b5cd4107acc28c8006645d7c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563547B2

Reaction notes

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