Reaktion #160791

Reaktionsgleichung

(4aR,8aR)-8a-hydroxyoctahydronaphthalen-1(2H)-one

aniline

Sodium triacetoxyborohydride

→

title compound

(4R,4aR,8aR)-4-(phenylamino)octahydronaphthalen-4a(2H)-ol

Lösungsmittel

CH3COOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for several hours
2. 2
   SonstigeThe mixture was then quenched with sat'd
3. 3
   Extraktionaq. NaHCO3 and extracted 3× with CH2Cl2
4. 4
   SonstigeThe combined organics were dried
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

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.

Quelle