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

4synthesis methods
71233-25-5 Synthesis
3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester

71233-25-5
150 suppliers
$6.00/1g

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Yield:220218-58-6 86%

Reaction Conditions:

with sodium borohydrid in methanol;water;

Steps:

33.B tert-butyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

EXAMPLE 33B tert-butyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate The product from Example 33A (10.84 g, 40 mmol) in methanol (200 mL) was treated with sodium borohydride (9.12 g, 240 mmol) slowly over 20 minutes at 0-10° C. The mixture was allowed to warm to ambient temperature and stirred for 20 hours. The mixture was concentrated under reduced pressure, treated with water (50 mL), and extracted with chloroform (2*10 mL). The organic phase was concentrated under reduced pressure to provide the title compound (8.0 g, 86% yield). 1H NMR (CD3OD, 300 MHz) δ 1.48 (s, 9H), 1.70-1.50 (m, 3H), 2.90-2.70 (m, 2H), 3.72-3.40 (m, 2H), 4.18-3.90 (m, 4H); MS (DCI/NH3) m/z 232 (M+H)+.

References:

US2002/19388,2002,A1