tert-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate synthesis

5synthesis methods

Product Name:tert-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate
CAS Number:849767-19-7
Molecular formula:C11H21NO4
Molecular Weight:231.29

161491-24-3 Synthesis

1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

161491-24-3
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tert-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

849767-19-7
15 suppliers
$65.00/10mg

Yield:849767-19-7 1900 mg

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0 - 60; for 2 h;

Steps:

130 Preparation of ferf-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-l-carboxylate

To a stirred solution of 1 -teri-butyl 3-methyl 4-oxopiperidine-l,3-dicarboxylate (2350 mg; 8.86 mmol)[l 61491-24-3] in methanol (50 mL) was added sodium borohydride (1030 mg; 26.6 mmol) at 0 °C. The reaction mixture was then heated to 60 °C and stirred for 2 hours. After cooling to room temperature, the reaction mixture was treated with IN HC1 aqueous solution (10 mL) and the product was extracted with diethyl ether (4 x 40 mL). The combined organic layers were dried over Na₂S0₄, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ether: acetone; 3:2; v/v) to afford feri-butyl 4-hydroxy-3-(hydroxymethyl)piperidine-l-carboxylate (1900 mg) as a yellow oil.

References:

WO2018/2220,2018,A1 Location in patent:Page/Page column 132-133

98977-34-5 Synthesis