Aluminium lithium hydride → (betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamine

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Reaction Steps

Lithium aluminum tetrahydride (730 mg, 20 mmol) was suspended in tetrahydrofuran (10 ml), then it was cooled in an ice-water bath and the solution of product of Example 5 (3 g, 9.2 mmol) in tetrahydrofuran (10 ml) was added dropwise. The reaction was carried out for 2 hours and quenched by adding 10% NaOH aqueous solution, Then the reaction solution was extracted with ethyl acetate for three times, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a pale yellow oil 2.7 g, yield: 93%. 1HNMR (300 MHz, CDCl3): δ 7.3-7.5 (5H, m), 7.2 (1H, t, J=7.6, 15.1), 6.8 (1H, d, J=8.5), 6.7 (2H, m), 5.0 (2H, s), 2.2-2.3 (2H, m), 2.2 (3H, s), 2.1 (3H, s), 1.8-1.9 (1H, m), 1.7-1.8 (1H, m), 1.5-1.6 (1H, m), 1.4-1.5 (1H, m), 1.0 (3H, d, J=6.2), 0.8 (3H, t, J=7.4, 14.7). ESI-MS: 312.3 (M+H).

Provenance & Evidence