Reaktion #160794

Reaktionsgleichung

{Benzyl[(1R,2R)-2-(1-ethoxyethenyl)-2-hydroxycyclohexyl]amino}acetonitrile

Ethanol

ethanol

→

title compound

(4aR,8aR)-1-benzyl-4,4-diethoxyoctahydroquinolin-4a(2H)-ol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred overnight
2. 2
   FiltrationThe reaction mixture was filtered through a pad of celite
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was purified by column chromatography (dry load) on silica gel
5. 5
   Wascheneluting with CH2Cl2/MeOH/NH3(Aq.)

Vorschrift

To silver nitrate (125 mg, 0.735 mmol) in Ethanol (27.00 ml) at room temperature was added {Benzyl[(1R,2R)-2-(1-ethoxyethenyl)-2-hydroxycyclohexyl]amino}acetonitrile (220 mg, 0.700 mmol) in 10 ml of absolute ethanol. The reaction mixture was stirred for an addition 1 hr. Another 125 mg of Silver Nitrate was added and the reaction was stirred overnight. The reaction mixture was filtered through a pad of celite, concentrated. The residue was purified by column chromatography (dry load) on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) to give the title compound. 1H-NMR (500 MHz, CDCl3) 2-4: δ 7.20-7.36 (m, 5H), 4.07 (d, 1H), 3.74 (dt, 1H), 3.62 (dt, 1H), 3.52 (dt, 1H), 3.41 (dt, 1H), 3.28 (bs, 1H), 3.06 (d, 1H), 2.61 (m, 1H), 2.00-2.14 (m, 2H), 1.88-1.98 (m, 2H), 1.70-1.80 (m, 2H), 1.54-1.62 (m, 2H), 1.22-1.44 (m, 2H), 1.18 (t, 6H). LRMS m/z (M+H) Calcd:334.5. found: 334.5.

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