(3S,4R)-1-BOC-3-HYDROXYMETHYL-4-(4-FLUOROPHENYL)-PIPERIDINE synthesis

10synthesis methods

Product Name:(3S,4R)-1-BOC-3-HYDROXYMETHYL-4-(4-FLUOROPHENYL)-PIPERIDINE
CAS Number:200572-33-4
Molecular formula:C17H24FNO3
Molecular Weight:309.38

923932-21-2 Synthesis

(3S,4R)-1-(tert-Butoxycarbonyl)-4-(4-fluorophenyl)-piperidine-3-carboxylic acid

923932-21-2
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(3S,4R)-1-BOC-3-HYDROXYMETHYL-4-(4-FLUOROPHENYL)-PIPERIDINE

200572-33-4
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$226.00/250mg

Yield:200572-33-4 94%

Reaction Conditions:

Stage #1: (-)-(3S,4R)-4-(4-fluoro-phenyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl esterwith dimethylsulfide borane complex in tetrahydrofuran at 0 - 20;
Stage #2: with methanol in tetrahydrofuran at 0;

Steps:

1.d

d) (3S,4R)-4-(4-Fluoro-phenyl)-3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester To a solution of (-)-(3S,4R)-4-(4-fluoro-phenyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1.71 g, 5.29 mmol) in 35 ml THF was added a 2 M borane dimethylsulfide complex solution in THF (5.44 ml, 10.9 mmol) at 0° C. The mixture was stirred for 15 min at 0° C. and then at room temperature over night. After cooling to 0° C. the reaction was quenched by the addition of methanol. Stirring was continued until no evolution of gas was observed any more. The reaction mixture was diluted with water and extracted with 3 portions of tert-butyl methyl ethyl. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash chromatography gave 1.58 g (94%) of the title compound as a colorless viscous oil. MS m/e (%): 310 (M+H⁺, 32)

References:

US2007/232652,2007,A1 Location in patent:Page/Page column 15

24424-99-5 Synthesis