Reaktion #1702078

Reaktionsgleichung

sodium triacetoxyborohydride

5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

acetic acid

2-(4-chlorophenyl)acetaldehyde

sodium bicarbonate

→

desired compound

Ausbeute 76.0%

1-(4-chlorophenethyl)-5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

Ausbeute 76.0%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with dichloromethane
2. 2
   TrocknenThe organic phases were dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated

Vorschrift

To a solution of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 in dichloroethane (2 ml) at 0° C. was added acetic acid (0.035 ml, 0.609 mmol), 2-(4-chlorophenyl)acetaldehyde (47.0 mg, 0.304 mmol) prepared as above and sodium triacetoxyborohydride (129.0 mg, 0.609 mmol). The mixture was stirred overnight at room temperature and then sodium bicarbonate was added followed by extraction with dichloromethane. The organic phases were dried over sodium sulfate, filtered and concentrated. Preparative thin layer chromatography (pentane/ethyl acetate: 1/1) of the obtained residue gave the desired compound as a yellow oil (59 mg, 76%).

Quelle