(S)-1-Cbz-3-(hydroxyMethyl)piperidine synthesis
- Product Name:(S)-1-Cbz-3-(hydroxyMethyl)piperidine
- CAS Number:405061-52-1
- Molecular formula:C14H19NO3
- Molecular Weight:249.31
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405061-52-1
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Yield:405061-52-1 70.4 %
Reaction Conditions:
with borane dimethyl sulfide in tetrahydrofuran at 0;Inert atmosphere;
Steps:
Step 1: benzyl (S)-3-(hydroxymethyl)piperidine-1-carboxylate:
To a stirred solution of (S)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid (1.50 g, 5.68 mmol, 1.00 equiv) in THF (15.0 mL) was added BH3-Me2S (1.7 mL, 4 M, 3.00 equiv) dropwise at 0 C under N2 atmosphere. The resulting mixture was stirred for 3 h at 0 C under N2 atmosphere. The reaction was quenched with water (30 mL) at 0 C and extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with EtOAc/PE (2/1) to afford benzyl (S)-3-(hydroxymethyl)piperidine-1-carboxylate (1.0 g, 70.4%) as a colorless oil. MS m/z: 250 [M+H]+.
References:
WO2022/232383,2022,A1 Location in patent:Paragraph 00310
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405061-52-1
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405061-52-1
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