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ChemicalBook CAS DataBase List 3-Piperidinemethanol,1-methyl-,(3R)-(9CI)
205194-11-2

3-Piperidinemethanol,1-methyl-,(3R)-(9CI) synthesis

3synthesis methods
-

Yield:205194-11-2 94%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water;

Steps:

13 EXAMPLE 13

A solution of (R)-ethyl 1-methylpiperidine-3-carboxylate (5.69 g, 33 mmol) in ether (20 ml) was added dropwise to a stirred solution of lithium aluminum hydride (36.6 ml of a 1M solution in THF, 36.6 mmol) in ether (85 ml) cooled to maintain a reaction temperature of 20° C. The mixture was stirred for 1.5 hours at ambient temperature and then water (1.4 ml), 15% aqueous sodium hydroxide solution (1.4 ml) and then water (4.3 ml) were added. The insolubles were removed by filtration and the volatiles removed from the filtrate by evaporation to give (R)-(1-methylpiperidin-3-yl)methanol (4.02 g, 94%) as a colourless oil. 1H NMR Spectrum: (DMSOd6) 1.06(q, 1H); 1.51-1.94(m, 5H); 2.04(s, 3H); 2.34(br s. 1H); 2.62(m, 1H); 2.78(d, 1H); 3.49(m, 1H); 3.59(m. 1H); MS-ESI: 130 [MH]+.

References:

US6414148,2002,B1

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