Water → 3-(1-Methylpiperidin-4-yl)propan-1-ol

To a refluxing solution of 1 M LiAlH4 (40 mmol) in THF (30 mL) was added dropwise a solution of N—BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol). The reaction mixture was heated for 3 h then cooled to rt. Upon further cooling to 0° C., water (1.5 mL) was added slowly, and the reaction mixture was allowed to warm to rt over 15 min. The mixture was again cooled to 0° C., and 10% aq. NaOH (1.5 mL) was added slowly. Upon warming to rt over 15 min, the mixture was cooled to 0° C. and more water (4.5 mL) was added. The resultant mixture was allowed to warm to rt over 18 h, and was then filtered through a pad of diatomaceous earth. The filtrate was concentrated, and the residue was purified by Method 1 to afford 1.9 g (100%) of 3-(1-methyl-piperidin-4-yl)-propan-1-ol as a yellow oil. MS (ESI): mass calcd for C9H19NO, 157.15; m/z found 158.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 3.45-3.41 (m, 2H), 2.77-2.74 (m, 2H), 1.89-1.85 (m, 2H), 1.64-1.61 (m, 2H), 1.47-1.43 (m, 2H), 1.21-1.12 (m, 5H).

1. temperatureThe reaction mixture was heated for 3 h
2. temperatureUpon further cooling to 0° C.
3. temperatureto warm to rt over 15 min
4. temperatureThe mixture was again cooled to 0° C.
5. temperatureUpon warming to rt over 15 min
6. temperaturethe mixture was cooled to 0° C.
7. temperatureto warm to rt over 18 h
8. filtrationwas then filtered through a pad of diatomaceous earth
9. concentrationThe filtrate was concentrated
10. customthe residue was purified by Method 1

ORD record

ord-e4d455becdda4344888717031956a019

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956066B2