Aniline → HCID 66577566, Verbindung

Reaktionsgleichung

[OH:1][C@@:2]12[C:11](=O)[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:6][CH2:5][CH2:4][CH2:3]2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O>[C:14]1([NH:13][C@H:11]2[C@:2]3([OH:1])[C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:8][CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Versuchsvorschrift

A mixture of (4aR,8aR)-8a-hydroxyoctahydronaphthalen-1(2H)-one (0.339 g, 2.015 mmol) and aniline (0.552 mL, 6.05 mmol) in 2% CH3COOH in ACE (20 mL) was stirred for 1 hr at rt. Sodium triacetoxyborohydride (1.37 g, 6.45 mmol) was then added and the mixture was stirred for several hours. The mixture was then quenched with sat'd. aq. NaHCO3 and extracted 3× with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography on silica gel to give the title compound. 1H NMR (500 MHz, CDCl3) δ 7.12-7.18 (m, 2H), 6.60-6.69 (m, 3H), 1.96-2.04 (m, 1H), 1.73-1.81 (m, 1H), 1.64-1.70 (m, 2H), 1.18-1.60 (m, 12H). HRMS (ES) m/z M+H calc'd: 246.1852. found: 246.1850.