Reaktion #51550

Reaktionsgleichung

1-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methylphenyl} ethanone

1-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methylphenyl}ethanone

sodium borohydride

→

title compound

1-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methylphenyl)ethanol

Lösungsmittel

ethyl acetate

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water and brine
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was purified by preparative HPLC (
5. 5
   WaschenC18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and the product
6. 6
   workup.ADDITIONcontaining fractions
7. 7
   Einengenwere concentrated, free-based with aq ammonium hydroxide
8. 8
   Extraktionextracted with chloroform
9. 9
   Waschenwashed with brine
10. 10
    Trocknendried (K2CO3)
11. 11
    Einengenconcentrated

Vorschrift

To a solution of 1-{2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-ylamino]-5-methylphenyl} ethanone from EXAMPLE 116 (20 mg, 0.05 mmol) in 5 ml methanol at 0° C. was added sodium borohydride (5.5 mg, 0.15 mmol). The solution was stirred with warming to room temperature for 2 h. The reaction was diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and the product containing fractions were concentrated, free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to afford the title compound of EXAMPLE 117 as a mixture of diastereomers at the alcohol center. LRMS (ES)+: 380.3 (M+H)+.

Quelle