(S)-Tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate synthesis

6synthesis methods

Product Name:(S)-Tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate
CAS Number:140645-22-3
Molecular formula:C11H20N4O2
Molecular Weight:240.31

191092-08-7
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(S)-Tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

140645-22-3
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Yield:140645-22-3 92%

Reaction Conditions:

with sodium azide;sodium iodide in N,N-dimethyl-formamide at 70; for 4 h;

Steps:

(S)-tert-butyl3-(azidomethyl)piperidine- 1 -carboxylate

(S)-tert-butyl3-(azidomethyl)piperidine- 1 -carboxylate._(S)-tert-butyl 3-((tosyloxy)methyl)piperidine-1 - carboxylate (8.85 g, 24 mmol) was dissolved in DMF (100 ml), and then NaN3 (6.24 g, 96 mmol) and Nal (0.36 g, 2.40 mmol) were added, followed by stirring at 70° C. for 4 hours. After the completion of the reaction, the reaction mixture was extracted with H20, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:10), to give (S)-tert-butyl 3-(azidomethyl)piperi- dine-i-carboxylate (5.38 g, 92%).‘H-NMR (300 MHz, CDC13) ? 4.09-3.82 (m, 2H),3.27-3.16 (m, 2H), 2.95-2.54 (m, 2H), 1.88-1.62 (m, 3H),1.52-1.42 (m, 1H), 1.47 (s, 9H), 1.30-1.20 (m, 1H)

References:

US2015/259350,2015,A1 Location in patent:Paragraph 0235; 0236