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

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

9synthesis methods

Product Name:N-BOC-4-METHYL-4-HYDROXY PIPERIDINE
CAS Number:406235-30-1
Molecular formula:C11H21NO3
Molecular Weight:215.29

676-58-4 Synthesis

676-58-4
287 suppliers
$15.00/25ml

79099-07-3 Synthesis

79099-07-3
543 suppliers
$5.00/5g

406235-30-1
118 suppliers
$22.00/250mg

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