tert-butyl ((3S,4S)-1-benzyl-4-fluoropiperidin-3-yl)carbamate synthesis

4synthesis methods

Product Name:tert-butyl ((3S,4S)-1-benzyl-4-fluoropiperidin-3-yl)carbamate
CAS Number:1052713-39-9
Molecular formula:C18H25FN2O4
Molecular Weight:352.4

13139-17-8
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tert-butyl N-[(3S,4S)-4-fluoropiperidin-3-yl]carbamate

1052713-48-0
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tert-butyl ((3S,4S)-1-benzyl-4-fluoropiperidin-3-yl)carbamate

1052713-39-9
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Yield:-

Reaction Conditions:

with triethylamine in tetrahydrofuran at 20; for 24 h;

Steps:

4.1 Step 1.

Triethylamine (0.19 mL, 1.37 mmol) was added to a solution of tert-butyl N-[(3S,4S)-4- fluoro-3-piperidyl]carbamate (250 mg, 1.15 mmol) in tetrahydrofuran (3 mL), followed by addition of N-(Benzyloxycabronyloxy) succinimide (430 mg, 1.73 mmol). The resulting reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate and quenched with saturated ammonium chloride solution, extracting with ethyl acetate twice. The combined organics were dried over magnesium sulfate and concentrated to produce the crude product, which was purified via silica gel column chromatography (0-40% ethyl acetate in hexanes) to yield benzyl (3S,4S)-3-(tert-butoxycarbonylamino)-4-fluoro-piperidine-1- carboxylate. ES/MS: m/z 353.74 [M+H]⁺.

References:

WO2021/222353,2021,A1 Location in patent:Page/Page column 377; 396

1-Piperidinecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-fluoro-, phenylmethyl ester

1214242-81-5
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(3R,4R)-benzyl 3-((tert-butoxycarbonyl)amino)-4-fluoropiperidine-1-carboxylate(WXFC0382)

1052713-38-8
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1052713-39-9
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References

24424-99-5 Synthesis

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References

66207-08-7
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References