Reaktion #1972971

Reaktionsgleichung

benzylamine

acetic acid

estra-1,3,5(10)-trien-17-one

THF

→

title compound

N-Benzylestra-1,3,5(10)-trien-17β-amine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   workup.ADDITIONdiluted with water (200 ml)
3. 3
   ExtraktionThe suspension was extracted with ethyl acetate (3×200 ml)
4. 4
   Trocknenthe combined extracts were dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to an oil
7. 7
   SonstigeThis product was chromatographed (300 g silica gel 0.4-4-96 Et3N-acetone-hexane, 20 ml fractions)
8. 8
   Sonstigegave impure product in fractions 53-79 and pure product in fractions 80-135
9. 9
   Sonstigeafter removal of the solvent

Vorschrift

To a solution of benzylamine (11.2 ml) in dry methanol (75 ml) was added sequentially acetic acid (6.16 ml), estra-1,3,5(10)-trien-17-one (5.21 g) sodium cyanoborohydride (1.35 g), and THF (60 ml) under a N2 atmosphere. The resulting mixture was stirred overnight at room temperature, concentrated in vacuo, diluted with water (200 ml), and made alkaline with aqueous sodium hydroxide (50 ml). The suspension was extracted with ethyl acetate (3×200 ml) and the combined extracts were dried over MgSO4, filtered and concentrated to an oil. This product was chromatographed (300 g silica gel 0.4-4-96 Et3N-acetone-hexane, 20 ml fractions) and gave impure product in fractions 53-79 and pure product in fractions 80-135. The latter were combined and after removal of the solvent gave the title compound as crystals, mp 71°-74° C. (PLA2, diabetes)

Quelle