(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE Chemical Properties

storage temp. 

2-8°C

Appearance

White to off-white Solid

(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE Usage And Synthesis

Uses

tert-Butyl (3S)-3-[(Methylsulfonyl)oxy]piperidine-1-carboxylate is used as a reactant in the synthesis of non-nucleoside MtbTMPK inhibitors.

Synthesis

Under nitrogen protection, (S)-1-Boc-3-hydroxypiperidine (10.0 g, 49.7 mmol) and triethylamine (7.82 mL, 54.7 mmol) were dissolved in dichloromethane (60 mL) and cooled to 0 °C. Subsequently, methanesulfonyl chloride (4.23 mL, 54.7 mmol) was slowly added dropwise and the reaction mixture was stirred at this temperature for 1 hour. Upon completion of the reaction, the reaction solution was diluted with deionized water (60 mL) and filtered through a hydrophobic glass stock. The organic layer was concentrated under reduced pressure to afford tert-butyl (3S)-3-(methylsulfonyloxy)piperidine-1-carboxylate (13.9 g, 49.7 mmol, 100% yield) as a colorless solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ (ppm) 4.76-4.71 (m, 1H, CH), 3.69-3.66 (m, 1H), 3.65-3.60 (m, 1H), 3.49-3.43 (m, 1H), 3.37-3.31 (m, 1H), 3.07 (s, 3H, CH3) , 2.02-1.96 (m, 1H), 1.94-1.91 (m, 1H), 1.87-1.80 (m, 1H), 1.59-1.53 (m, 1H), 1.48-1.45 (m, 9H).

References

[1] Patent: WO2014/188173, 2014, A1. Location in patent: Paragraph 00224
[2] Patent: CN105399756, 2016, A. Location in patent: Paragraph 0152; 0167-0168
[3] MedChemComm, 2014, vol. 5, # 12, p. 1879 - 1886
[4] Patent: WO2017/134684, 2017, A2. Location in patent: Page/Page column 12
[5] Patent: CN103864673, 2016, B. Location in patent: Paragraph 0084; 0085

(S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE(940890-90-4)Related Product Information

• (S)-1-Boc-3-hydroxypiperidine
• 1-METHYLPIPERIDIN-3-YL METHANESULFONATE
• N-BOC-3-MESYLOXYPIPERIDINE
• (S)-1-(TERT-BUTOXYCARBONYL)PIPERIDIN-3-YL METHANESULFONATE