TERT-BUTYL [5-(HYDROXYMETHYL)PYRIDIN-2-YL)CARBAMATE Chemical Properties

Boiling point:

332.8±32.0 °C(Predicted)

Density 

1.209

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

12.35±0.70(Predicted)

Appearance

White to off-white Solid

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

HS Code 

29309090

TERT-BUTYL [5-(HYDROXYMETHYL)PYRIDIN-2-YL)CARBAMATE Usage And Synthesis

Chemical Properties

White solid

Synthesis

To a stirred solution of ethyl 6-(tert-butoxycarbonylamino)nicotinate (100; 10.0 g, 27.3 mmol) in tetrahydrofuran (THF) (40 mL) was slowly added a solution of lithium aluminum hydroxide (LA1H4) (1.92 g, 50.5 mmol) in THF (60 mL) over 30 min, keeping the reaction temperature not below 0 °C. The reaction mixture was continued to be stirred at 0 °C for 6 hours. Upon completion of the reaction, water (1.0 mL) and 10% sodium hydroxide (NaOH) solution (2.0 mL) were carefully added at 0 °C to quench the reaction. The resulting mixture was filtered and the filtrate was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (eluent ratio dichloromethane: methanol = 40:1) to afford the target product tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate 101 (4.50 g, 74% yield).

References

[1] Patent: WO2010/3048, 2010, A1. Location in patent: Page/Page column 110
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 1151 - 1175
[3] Patent: WO2014/52365, 2014, A1. Location in patent: Page/Page column 257-258
[4] Patent: US6046190, 2000, A
[5] Patent: US5968942, 1999, A

TERT-BUTYL [5-(HYDROXYMETHYL)PYRIDIN-2-YL)CARBAMATE(169280-83-5)Related Product Information

• METHYL 6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINATE
• 2-(BOC-AMINO)-5-PICOLINE
• (5-METHOXYMETHYL-PYRIDIN-2-YL)-CARBAMIC ACID TERT-BUTYL ESTER
• TERT-BUTYL [5-(HYDROXYMETHYL)PYRIDIN-2-YL)CARBAMATE
• 6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINIC ACID