Sodium borohydride → Tert-butyl [1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]carbamate

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Reaktionsgleichung

[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11](=[O:22])[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:6][CH:5]=1.P([O-])(O)(O)=O.[Na+]>CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:11]([OH:22])[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:6][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

tert-Butyl 4[1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]carbamate 0.314 g (8.3 mmol) of sodium borohydride was added in 4 portions to a solution of 3.16 g (8.3 mmol) of tert-butyl [1-(4-fluorophenyl)-2-oxo-2-quinolin-8-ylethyl]carbamate in 45 ml of methanol at 0-5° C. The reaction mixture was stirred at 0-5° C. for 0.5 h and then at room temperature for 0.5 h and subsequently poured into an aqueous sodium dihydrogen phosphate solution (80 g/l). Extraction twice with ethyl acetate was followed by drying on magnesium sulfate. Concentration resulted in 2.78 g of tert-butyl [1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]carbamate (diastereoisomer mixture: 80/20) as pale yellow powder (yield: 88%).

Aufarbeitung

waitat room temperature for 0.5 h
extractionExtraction twice with ethyl acetate
customby drying on magnesium sulfate
concentrationConcentration

Quellen und Nachweise

ORD-Eintrag: ord-65edd13b815246ee95e645917eb003c3
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07825264B2

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