Reaction #81816

Reaction equation

5,11-dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

methoxylamine hydrochloride

diisopropylethylamine

→

title compound

Yield 31.4%

5,11-Dihydro-11-ethyl-6-methoxyimino-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

Yield 31.4%

Solvents

methylene chloride

Conditions

Workup

1. 1
   WashThe organic phase was washed with water
2. 2
   Otherdried
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe solution was concentrated in vacuo
5. 5
   Otherthe residue was chromatographed over silica with 20% ethyl acetate/hexane

Procedure

A solution of 5,11-dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine (0.3 g, 0.75 mmol), methoxylamine hydrochloride (0.15 g, 1.8 mmol) and diisopropylethylamine (0.3 g, 2 mmol) in methylene chloride was stirred at room temperature for 4 days. The organic phase was washed with water, dried, and filtered. The solution was concentrated in vacuo and the residue was chromatographed over silica with 20% ethyl acetate/hexane to give 0.07 g of the title compound, m.p. 164°-166° C.

Source