Reaktion #410350

Reaktionsgleichung

4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonyl-5-hexenyloxy)phenyl]benzamide

sodium borohydride

→

4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonylhexyloxy)phenyl]benzamide

Ausbeute 94.1%

Lösungsmittel

methanol

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a bed of Celite
2. 2
   Einengenconcentrated
3. 3
   workup.ADDITIONThe residue was diluted with ethyl acetate
4. 4
   Waschenwashed with water and brine
5. 5
   TrocknenThe organic layer was dried over magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonyl-5-hexenyloxy)phenyl]benzamide (360 mg) and nickel chloride hexahydrate (594 mg) in methanol (15 ml) and tetrahydrofuran (15 ml) was treated at 0° C. with sodium borohydride (283 mg) and stirred at 0° C. for 4 hours. The reaction mixture was diluted with tetrahydrofuran and filtered through a bed of Celite and then concentrated. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, concentrated to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonylhexyloxy)phenyl]benzamide (340 mg).

Quelle