Potassium tert-butoxide → 4-(7-Trifluoromethyl-benzo[d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2111733

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2F)=[N:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a room temperature mixture of 4-[(2-fluoro-3-trifluoromethyl-phenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.40 g, 3.59 mmol) in THF (20 mL) under nitrogen was added potassium tert-butoxide (3.60 mL of a 1M THF solution, 3.60 mmol) in one portion and the reaction heated at 60° C. for 1.5 h. After standing at room temperature overnight, the solvent was removed and the residue diluted with ethyl acetate (60 mL). The organics were washed with water (30 mL) and brine (30 mL) successively, dried over magnesium sulfate, filtered, and concentrated to give an amber solid. The crude product was chromatographed on silica using 40% ethyl acetate/heptane as eluent to afford 0.97 g (73%) of the desired product as a white solid, mp: 111-113° C.

Aufarbeitung

customthe solvent was removed
additionthe residue diluted with ethyl acetate (60 mL)
washThe organics were washed with water (30 mL) and brine (30 mL) successively
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give an amber solid
customThe crude product was chromatographed on silica using 40% ethyl acetate/heptane as eluent

Quellen und Nachweise

ORD-Eintrag: ord-42459509d7e6493098e6d203be48e45c
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07521445B2

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