Aluminium lithium hydride → 3(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine, (2R,3R)-

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Reaction Steps

Lithium aluminum tetrahydride (730 mg, 20 mmol) was suspended in tetrahydrofuran (10 ml), after the mixture was cooled in an ice-water bath, the solution of product of Example 15 (2.2 g, 9.0 mmol) in tetrahydrofuran (10 ml) was added dropwise, then the reaction was carried out for 2 hours, and quenched by adding 10% NaOH aqueous solution, after the reaction solution was extracted with ethyl acetate for three times, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a pale yellow oil 1.9 g, yield: 90%. 1HNMR (300 MHz, CDCl3): δ 7.2 (1H, t, J=7.9, 15.6), 6.6-6.8 (3H, m), 3.7 (3H, 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=6.3), 0.8 (3H, t, J=7.4, 14.5). ESI-MS: 236.3 (M+H).

Provenance & Evidence