N-BOC-3-MESYLOXYPIPERIDINE Chemical Properties

Melting point:

67-70°

Boiling point:

407.2±34.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-3.34±0.40(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C11H21NO5S/c1-11(2,3)16-10(13)12-7-5-6-9(8-12)17-18(4,14)15/h9H,5-8H2,1-4H3

InChIKey

WLAZHMYDLUILKR-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC(OS(C)(=O)=O)C1

N-BOC-3-MESYLOXYPIPERIDINE Usage And Synthesis

Synthesis

Step 1. To a stirred solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (5 g, 24.84 mmol) and triethylamine (5.027 g, 6.924 mL, 49.68 mmol) in dichloromethane (50 mL) was slowly added methanesulfonyl chloride (3.130 g, 2.115 mL, 27.32 mmol) under the conditions of an ice bath at 0°C. The reaction mixture was gradually warmed to room temperature over 3 hours. Upon completion of the reaction, the reaction mixture was washed with water and 1 M hydrochloric acid, followed by drying with magnesium sulfate, filtration and concentration in vacuum to afford tert-butyl 3-((methanesulfonyl)oxy)piperidine-1-carboxylate as a yellow oil (7.9 g, quantitative yield, with a small amount of residual solvent).1H NMR (400.0 MHz, CDCl3) δ 1.49 (s, 9H), 1.60- 1.57 (m, 1H), 2.04-1.79 (m, 3H), 3.08 (s, 3H), 3.38-3.32 (m, 1H), 3.50-3.43 (m, 1H), 3.70-3.60 (m, 2H) and 4.74 (br s, 1H) ppm.

References

[1] Patent: US2013/115310, 2013, A1. Location in patent: Paragraph 0248; 0249
[2] Patent: US2016/168156, 2016, A1. Location in patent: Paragraph 0485; 0486
[3] Carbohydrate Research, 1990, vol. 204, # 1, p. 11 - 25
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4334 - 4343
[5] Patent: US2017/305920, 2017, A1. Location in patent: Paragraph 0151; 0152

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