Reaktion #1702080

ord-e803529905e74d3794b9fc2f21ac6749

Reaktionsgleichung

ClCCl
dichloromethane
CC(C)=O
acetone
COc1ccc2c(c1)CN(C1CC1)C(=O)CCN2CC(=O)c1ccc(F)cc1
5-cyclopropyl-1-(2-(4-fluorophenyl)-2-oxoethyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one
[BH4-].[Na+]
sodium borohydride
COc1ccc2c(c1)CN(C1CC1)C(=O)CCN2CC(O)c1ccc(F)cc1
desired product
Ausbeute 46.0%
COc1ccc2c(c1)CN(C1CC1)C(=O)CCN2CC(O)c1ccc(F)cc1
5-cyclopropyl-1-(2-(4-fluorophenyl)-2-hydroxyethyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one
Ausbeute 46.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe resulting solution was washed with water
  2. 2
    Trocknenthe organic phase was dried over sodium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    SonstigeEvaporation

Vorschrift

To a solution of 5-cyclopropyl-1-(2-(4-fluorophenyl)-2-oxoethyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (65.0 mg, 0.170 mmol) from Example 5 in ethanol (1 ml) was added sodium borohydride (6.4 mg, 0.170 mmol) and the reaction mixture was stirred at room temperature over weekend. Then was added acetone (0.062 ml) followed by dilution with dichloromethane. The resulting solution was washed with water and the organic phase was dried over sodium sulfate and filtered. Evaporation gave the desired product (30 mg, 46%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08765728B2uspto-grants-2014_07