(6-methylpiperidin-3-yl)methanol synthesis

Yield:-

Reaction Conditions:

Stage #1:methyl 6-methylpiperidine-3-carboxylate.hydrochloride with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 22;
Stage #2: with water;sodium hydroxide in tetrahydrofuran

Steps:

A
A suspension of the amine hydrochloride, ~3:1 trans:cis (500 mg, 2.58 mmol) in THF (15 ml) was treated slowly with lithium aluminum hydride (3.37 ml, 7.75 mmol) at 22 ⁰C. The solution was warmed to 0 ⁰C and stirred for 20 min, then treated, dropwise with 0.294 mL of water, 0.294 ml of 15% NaOH, and 0.882 mL of water successively. Sodium sulfate was added to the mixture. After stirring 20 min at 22 ⁰C, the mixture was filtered and the filtrate was concentrated to yield A-4. as a colorless oil. Data for A-4: LRMS m/z (M+H): 130.2.

References:

MERCK SHARP & DOHME CORP.;BRESLIN, Michael, J.;COLEMAN, Paul, J.;COX, Christopher, D.;SCHREIER, John, D.;WHITMAN, David, B. WO2010/48010, 2010, A1 Location in patent:Page/Page column 36-37