tert-butyl 4-(4-(hydroxymethyl)phenyl)piperidine-1-carboxylate synthesis
- Product Name:tert-butyl 4-(4-(hydroxymethyl)phenyl)piperidine-1-carboxylate
- CAS Number:864359-18-2
- Molecular formula:C17H25NO3
- Molecular Weight:291.39
149353-75-3
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Yield:864359-18-2 92%
Reaction Conditions:
Stage #1: 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acidwith borane-THF in tetrahydrofuran at 20;
Stage #2: with water;ammonium chloride in tetrahydrofuran;
Steps:
42
Synthesis of 4-(4-hydroxymethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1). A solution of N-Boc-4-(4-carboxyphenyl) piperidine (305 mg, 1.0 mmol) and 1 M BH3 THF (3.1 ml, 3.1 mmol) in THF (3 ml) was maintained under nitrogen at ambient temperature overnight. Reaction was quenched with 5% aq. NH4Cl (5 ml) and extracted with EtOAc (30 ml x 2). Organic layer was washed with 5% NaHCO3 (20 ml) and brine (20 ml) and dried over MgSO4. Solvent was evaporated in vacuum. Residue was dried in vacuum overnight to provide target compound (1) (272 mg, 93%) as white solid. LC-MS [M+H] 292.3 (C17H25NO3+H, requires 292.40).
References:
WO2008/154642,2008,A2 Location in patent:Page/Page column 151-152
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864359-18-2
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