HCID 19021731, compound → HCID 10421359, compound

Participants

Reaction Conditions

Reaction Steps

Part B. A slurry of lithium aluminum hydride (5.50 g, 145 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., and a solution of the amide prepared in Part A (11.48 g, 47.2 mmol) in tetrahydrofuran (50 mL) was added dropwise over 1 hour. The ice bath was removed, and the mixture was heated to reflux for 18 hours. After cooling to 0° C., the mixture was quenched by the slow dropwise addition of water (6 mL), aq. NaOH (18 mL, 15%), and water (18 mL). The solution was filtered through a plug of Celite®, dried over potassium carbonate, and concentrated under vacuum to afford N-heptyl-3,3-dimethyl-5-hydroxypentanamine as a clear, colorless oil (7.61 g, 33.2 mmol, 70%). 1H NMR (CDCl3) δ3.70(dt,2H,J=10.2,7.0Hz); 2.70-2.55(m,2H); 2.39-2.29(m,2H); 1.56(dt,2H,J=12.1,7.0Hz); 1.51-1.41(m,6H); 1.36-1.24(m,8H); 0.91(s,6H); 0.88(t,3H,J=6.9Hz).

Provenance & Evidence