Sodium borohydride → HCID 67075178, Verbindung

Reaktionsgleichung

[BH4-].[Na+].[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1>[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]([CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

Versuchsvorschrift

Sodium borohydride (12 mg, 0.34 mmol) and 2 drops methanol were added to a solution of [(4-methoxy-phenyl)-(4-oxo-cyclohexyl)-methyl]-carbamic acid tert-butyl ester (33, 110 mg) in THF (5 mL). After stirring for 7 hours the reaction was worked up by washing the solution with saturated sodium bicarbonate solution and brine. After drying the organic phase over sodium sulphate, followed by filtration, evaporation gave 101 mg of the desired cis/trans isomer mixture (34) as a colourless solid, which was used directly in the next stage. Rt=1.36, 1.39 min (Method 5). Detected mass: 219.2 (M—C4H8—CO2—H2O+).