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ChemicalBook CAS DataBase List N-BOC-4-METHYL-4-HYDROXY PIPERIDINE

N-BOC-4-METHYL-4-HYDROXY PIPERIDINE synthesis

9synthesis methods
-

Yield:406235-30-1 99%

Reaction Conditions:

in tetrahydrofuran at -78 - 0; for 2 h;

Steps:

70.A Step A:
tert-butyl 4-hydroxy-4-methylpiperidine-1-carboxylate

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (1.00 g, 5.02 mmol) in dry THF (25 mL) was added methylmagnesium chloride (2.17 mL, 6.52 mmol) at -78° C.
The reaction mixture was slowly warmed to 0° C. with stirring for 2 hours and quenched with saturated aq. NH4Cl.
The mixture was extracted with EtOAc twice, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford tert-butyl 4-hydroxy-4-methylpiperidine-1-carboxylate (1.08 g, >99%) as a colorless oil, which was used for the next reaction without further purification. 1H-NMR (CDCl3, Varian, 400 MHz): δ 1.27 (3H, s), 1.46 (9H, s), 1.50-1.58 (4H, m), 3.20-3.27 (2H, m), 3.64-3.76 (2H, m).

References:

US2016/168156,2016,A1 Location in patent:Paragraph 0602; 0603

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