Iodine → 1-[[(1S)-1-(4-Bromophenyl)ethyl]amino]-5-methyl-3-(1-methylethyl)-5-hexen-3-ol

Participants

Reaction Steps

To a suspension of Mg (11 g, 458 mmol) and I2 (0.5 g) in anhydrous tetrahydrofuran (50 mL) was added 3-chloro-2-methylprop-1-ene (1 mL) to initiate the reaction. Tetrahydrofuran (300 mL) was added, more solution of 3-chloro-2-methylprop-1-ene (15 mL) in tetrahydrofuran (20 mL) was dropped into the reaction at 0° C. under N2 over 30 min A solution of 1-[(S)-1-(4-bromophenyl)-ethylamino]-4-methyl-pentan-3-one (5 g) in tetrahydrofuran (50 mL) was added dropwise at −78° C. over 45 min. The reaction mixture was stirred at room temperature for 2 h. The reaction was cautiously quenched with saturated aqueous NH4Cl, and the reaction mixture was filtered. The filtrate was extracted with EtOAc (3×100 mL) and the combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give 3-{(S)-2-[1-(4-bromophenyl)-ethylamino]-ethyl}-2,5-dimethyl-hex-5-en-3-ol (6.4 g, 90% yield), which was used for the next step without further purification.

Provenance & Evidence