Hydrazine hydrate (1:1) → N-(3-Phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline

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Reaction Steps

Compound 23 (2.00 g, 0.0038 mol) and hydrazine hydrate (1.02 mL, 21.0 mmol) were dissolved in ethanol (100 mL) and refluxed overnight. The solution was then cooled, and the white precipitate was filtered and washed with cold ethanol. The solution was concentrated under reduced pressure and the crude material taken up in 3:1, CH2Cl2/THF (100 mL). The resulting white precipitate was filtered and washed with cold CH2Cl2 (50 mL). The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield crude product. The crude product was purified by flash chromatography (40% CMA 80 in CHCl3) to afford 1.45 g (97%) of 24 as a colorless oil: LCMS (APCI): m/z 393.8 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 7.14-7.30 [m, 8H], 6.70-6.74 [m, 1H], 3.86 [s, 3H], 3.05 [m, 1H], 2.77-2.79 [br m, 1H], 2.65 [ddd, J1=J2=9 Hz, J3=3 Hz, 2H], 2.58 [d, J=12 Hz, 1H], 2.26-2.36 [m, 4H], 2.04-2.12 [m, 3H], 1.68-1.81 [m, 4H], 1.44-1.50 [m, 4H], 1.32 [m, 1H], 1.21 [s, 3H]; 13C NMR (CDCl3, 300 MHz) δ 159.2, 150.3, 142.9, 128.9, 128.6, 128.5, 126.0, 121.8, 116.5, 110.0, 62.6, 58.2, 55.5, 51.3, 46.9, 44.5, 43.2, 36.7, 36.3, 34.0, 32.1, 29.2, 25.8.

Provenance & Evidence