Reaktion #51882

Reaktionsgleichung

sodium borohydride

N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene]amine

tetrahydrofuran

methanol

→

title compound

Ausbeute 54.0%

trans-N-Benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]amine

Ausbeute 54.0%

Lösungsmittel

diethyl ether

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a flask equipped with magnetic stirrer
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGAfter stirring for 10 min
4. 4
   Sonstigethe layers were separated
5. 5
   Extraktionthe aqueous layer extracted with dichloromethane (3×100 ml)
6. 6
   WaschenThe combined organic phases were washed with brine (50 ml)
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigePurification via FCC (
10. 10
    WaschenSiO2, ethyl acetate/petroleum ether, gradient elution

Vorschrift

To a flask equipped with magnetic stirrer was added N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene]amine (4.00 g, 7.63 mmol) and tetrahydrofuran (480 ml) followed by methanol (120 ml). To the solution was added sodium borohydride (1.16 g, 30.5 mmol) and the reaction mixture stirred for 17 hr. The reaction mixture was then diluted with diethyl ether (600 ml) and aqueous sodium hydroxide (400 ml, 0.4M) was added. After stirring for 10 min, the layers were separated and the aqueous layer extracted with dichloromethane (3×100 ml). The combined organic phases were washed with brine (50 ml), dried over magnesium sulfate and concentrated in vacuo. Purification via FCC (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:9, 1:4, then 3:7, v/v) furnished the title compound as a cream solid (2.09 g, 54%). δH(CDCl3) 0.01 (6H, s), 0.05 (6H, s), 0.80 (9H, s), 0.85 (9H, s), 1.18 (4H, m), 1.66 (2H, m), 1.87 (2H, m), 2.19 (1H, m), 2.68 (1H, M), 6.12 (1H, d), 6.23 (1H, dd), 6.77 (1H, d), 7.17 (5H, m).

Quelle