tert-butyl 3-(cyanoMethyl)piperidine-1-carboxylate synthesis
- Product Name:tert-butyl 3-(cyanoMethyl)piperidine-1-carboxylate
- CAS Number:948015-72-3
- Molecular formula:C12H20N2O2
- Molecular Weight:224.3
162166-99-6
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Yield:948015-72-3 327 mg
Reaction Conditions:
with sodium cyanide in dimethyl sulfoxide at 100; for 2.5 h;
Steps:
1 tert-butyl 3-(cyanomethyl)piperidine-1-carboxylate (37)
15The compound 36 (542 mg, 1.84 mmol, 1 eq) and NaCN (135 mg, 2.76 mmol, 1.5 eq) are dissolved in 6.4 mL DMSO, and then heated at 100 C for 2.5 hours. After cooling down, it is diluted with Et2O, washed with water, brine, dried over Na2SO4. Filtration and concentration afford the crude cyanide 61 (327 mg, 79%) slightly yellow oil, which is used in the next step without further purifications. 1H NMR (400 MHz, Chloroform-d) d 3.92 (d, J = 13.2 Hz, 1H), 3.81 (dt, J = 13.5, 4.4 Hz, 1H), 2.91 (ddd, J = 13.5, 10.3, 3.2 Hz, 1H), 2.83-2.67 (m, 1H), 2.30 (qd, J = 16.9, 6.6 Hz, 2H), 1.90 (dddq, J = 19.9, 9.9, 6.5, 3.8, 3.3 Hz, 2H), 1.67 (ddt, J = 12.6, 8.2, 4.2 Hz, 1H), 1.56-1.48 (m, 1H), 1.45 (s, 9H), 1.43-1.23 (m, 1H). HRMS (ESI) : m/z [M+H]+ calcd. for C12H21N2O2: 225.15 found: 225.16
References:
WO2021/53158,2021,A1 Location in patent:Page/Page column 30; 45
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