HCID 19021731, compound → HCID 10421359, compound

Temperature

0 °C

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).

1. additionwas added dropwise over 1 hour
2. customThe ice bath was removed
3. temperaturethe mixture was heated
4. temperatureto reflux for 18 hours
5. customthe mixture was quenched by the slow dropwise addition of water (6 mL), aq. NaOH (18 mL, 15%), and water (18 mL)
6. filtrationThe solution was filtered through a plug of Celite®
7. dry with materialdried over potassium carbonate
8. concentrationconcentrated under vacuum

ORD record

ord-db1174f48f724a08b8a61f8d3561c677

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166214