tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate Chemical Properties

Boiling point:

341.0±27.0 °C(Predicted)

Density 

1.124

storage temp. 

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

pka

12.48±0.20(Predicted)

form 

Solid

color 

Off-white

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

InChI

InChI=1S/C11H22N2O3/c1-10(2,3)16-9(14)13-6-4-11(15,8-12)5-7-13/h15H,4-8,12H2,1-3H3

InChIKey

XYWCDAFPRBDRER-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(CN)(O)CC1

CAS DataBase Reference

392331-66-7

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate Usage And Synthesis

Uses

4-Aminomethyl-1-Boc-4-hydroxypiperidine can be used in agrochemical, pharmaceutical and dyestuff.

Synthesis

General procedure for the synthesis of tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate from tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate: In a 100 mL sealed tube, a magnetic stirring bar, tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (300 mg, 1.28 mmol) and 7 M ammonium hydroxide in a methanol solution (20 mL). The reaction mixture was placed in an oil bath at 80°C and stirred for 16 hours. After completion of the reaction, the mixture was cooled to room temperature. The solvent was removed by concentration under reduced pressure to afford the crude product tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate (350 mg, >95% yield), which could be used in the subsequent reaction without further purification.LCMS (ESI) m/z 231 [M + H]+.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7458 - 7461
[2] Patent: US2016/185786, 2016, A1. Location in patent: Paragraph 0679
[3] Patent: WO2015/92804, 2015, A1. Location in patent: Page/Page column 21
[4] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 289 - 301
[5] Patent: WO2014/147636, 2014, A1. Location in patent: Page/Page column 35; 36

tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate(392331-66-7)Related Product Information

• 4-Aminomethyl-1-Boc-piperidin-4-ol hydrochloride
• tert-butyl 4-(7-chloro-2-oxo-2,3-dihydro-1H-indol-3-ylidene) piperidine-1-carboxylate
• tert-butyl 4-(7-bromo-4-methylquinazolin-2-yl)piperidine-1-c arboxylate
• tert-butyl 4-(aminomethyl)-2,2,4-trimethylpyrrolidine-1-carb oxylate
• 1-N-BOC-4-AMINOMETHYL-4-PHENYLPIPERIDINE
• DL-Pipecolinic acid