Reaktion #1597626

Reaktionsgleichung

Sodium borohydride

2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

→

cis-2,2,2-trifluoro-N-(-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe volatiles were removed in vacuo
2. 2
   Sonstigethe crude material purified by silica gel chromatography
3. 3
   Wascheneluting with 5% methanol in dichloromethane

Vorschrift

Sodium borohydride (20 mg, 0.51 mmol) was added to a solution of 2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide (140 mg, 0.51 mmol) in anhydrous methanol (4 mL). After stirring overnight, the volatiles were removed in vacuo and the crude material purified by silica gel chromatography, eluting with 5% methanol in dichloromethane furnished as the first eluting isomer cis-2,2,2-trifluoro-N-(-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide; (60 mg, 0.22 mmol) 1H-NMR (300 MHz, CDCl3) δ 7.34 (d, 1H), 7.01-6.82 (m, 3H), 5.35 (m, 1H), 5.15 (m, 1H), 3.82 (s, 3H), 2.87 (m, 1H), 1.93 (m, 1H).

Quelle