Lithium borohydride → β-Amino-β-butylbenzenepropanol

Participants

Reaction Steps

To a solution of methyl ester (0.13 g, 0.55 mmol) from step B in 7.8 mL THF was added LiBH4 (2.3 mL, 4.6 mmol, 2M in THF). After 2 h at reflux, the reaction was cooled to rt and quenched by the dropwise addition of MeOH, followed by acetone. After the volatiles were removed in vacuo, the remaining residue was redissolved in 23 mL 1N HCl and heated to 45° C. for 1.5 h. The volatiles were removed in vacuo, and the remaining residue was redissolved in saturated aqueous NaHCO3. The aqueous layer was extracted with CHCl3 (4×), the combined organics layers were dried over Na2SO4, filtered and concentrated to afford 2-amino-2-benzylhexan-1-ol II which was used for the next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ 7.32-7.18 (m, 5H), 3.32 (m, 2H), 7.70 (m, 2H), 1.53-1.31 (m, 6H), 0.93 (t, J=6.8 Hz, 3H) LCMS M+H=208.

Provenance & Evidence