Hydrochloric Acid → HCID 21955378, compound

Temperature

60 °C

Lithium borohydride (500 mg, 22.7 mmol) was added to a solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 4-(3-hydroxypropyl)-1,4-piperidinedicarboxylate (Description 136, 1.05 g, 2.79 mmol) in tetrahydrofuran/toluene (50:50, 20 mL). and the mixture was stirred at 60° C. for 4 hours. The mixture was cooled and hydrochloric acid (2M, 10 mL) was added. The mixture was poured into aqueous sodium carbonate (10%, 100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/MeOH (100:0 increasing to 95:5) to give the title compound (563 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 3.67 (2H, t, J 7 Hz), 3.48 (2H, s), 3.47–3.40 (2H, m), 3.35–3.25 (2H, m), 1.7 (2H, br s), 1.6–1.3 (8H, m), and 1.44 (9H, s).

1. temperatureThe mixture was cooled
2. extractionextracted with ethyl acetate (3×50 mL)
3. dry with materialThe combined organic fractions were dried (Na2SO4)
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel
6. washeluting with EtOAc/MeOH (100:0 increasing to 95:5)

ORD record

ord-0d1505ab055046c289016d2437e9cf33

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105507B2