(3R,5S)-tert-butyl 3-aMino-5-fluoropiperidine-1-carboxylate synthesis
- Product Name:(3R,5S)-tert-butyl 3-aMino-5-fluoropiperidine-1-carboxylate
- CAS Number:1271810-13-9
- Molecular formula:C10H19FN2O2
- Molecular Weight:218.27
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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Yield: 76%
Reaction Conditions:
with hydrogen in tetrahydrofuran at 20; for 16 h;
Steps:
31
To a solution of(3R,5S)-ieri-butyl 3-azido-5-fluoropiperidine-l -carboxylate 31.12 (1.0 eq) in THF (20 eq) at rt was added Raney-Ni (100% w/w). The mixture was flushed with H2 for 2 times, stirred at rt for 16 h, and filtered. The filtrate was concentrated in vacuo to get the crude product, which was triturated with petroleum ether to afford the desired compound 31.13, (76% yield), as a white solid. LCMS m/z 163.1 [M-'Bu+H] +, and 219.0 [M+H] +. 1H NMR (400 MHz, DMSO-i¾) δ: 4.83 (d, J = 37.6 Hz, 1H), 4.03-3.97 (m, 1H), 3.96-3.86 (m, 1H), 2.96-2.88 (m, 1H), 2.80 (bs, 1H), 2.46-2.29 (m, 1H), 2.07-2.01 (bs, 1H), 1.51 (s, 2H, -NH2), 1.39 (s, 9H), 1.36-1.23 (m, 1H).
References:
BIOGEN IDEC MA INC.;ERLANSON, Daniel, A.;MARCOTTE, Doug;KUMARAVEL, Gnanasambandam;FAN, Junfa;WANG, Deping;CUERVO, Julio, H.;SILVIAN, Laura;POWELL, Noel;BUI, Minna;HOPKINS, Brian, T.;TAVERAS, Art;GUAN, Bing;CONLON, Patrick;ZHONG, Min;JENKINS, Tracy, J.;SCOTT, Daniel;SUNESIS PHARMACEUTICALS, INC.;LUGOVSKOY, Alexey, A. WO2011/29046, 2011, A1 Location in patent:Page/Page column 153; 157
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