1-(tert-Butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine Chemical Properties

Boiling point:

303℃

Density 

1.035

Flash point:

137℃

storage temp. 

2-8°C

pka

-1.51±0.40(Predicted)

form 

solid

color 

off white

InChI

InChI=1S/C12H21NO3/c1-11(2,3)16-10(15)13-7-6-9(14)12(4,5)8-13/h6-8H2,1-5H3

InChIKey

MXCAGVCUIHYAGH-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(=O)C(C)(C)C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

1-(tert-Butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine Usage And Synthesis

Uses

1-(tert-Butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine can be used as organic synthesis intermediates and pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of 1-BOC-3,3-dimethyl-4-oxopiperidine from di-tert-butyl dicarbonate and 3,3-dimethyl-1-phenylmethyl-piperidin-4-one: 10.14 g (46.66 mmol) of 1-benzyl-3,3-dimethyl-4-oxo-piperidine, 1.03 g of 10% palladium-carbon catalyst and 11.09 g (50.81 mmol) of di- di-tert-butyl carbonate were dissolved in 210 mL of methanol. The mixture was purged three times with nitrogen and then three times with hydrogen. Subsequently, the mixture was subjected to 50 psig hydrogen pressure and the reaction was shaken at room temperature for 16 hours. Upon completion of the reaction, the reaction mixture was filtered through a bed of diatomaceous earth and glass microfiber filter paper. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as eluent. The elution grade containing the target product was collected and concentrated under reduced pressure to give 9.38 g (88.5% yield) of 1-(tert-butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine.

References

[1] Patent: EP1204659, 2003, B1. Location in patent: Page/Page column 27
[2] Patent: EP1204660, 2004, B1. Location in patent: Page 18
[3] Patent: EP1204660, 2004, B1. Location in patent: Page 16-17
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1627 - 1629
[5] Patent: US2002/169155, 2002, A1

1-(tert-Butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine(324769-06-4)Related Product Information

• tert-butyl 4-glycyl-1-piperazinecarboxylate(SALTDATA: HCl 0.95H2O)
• 1-BOC-4-AMINOMETHYL-PIPERIDINE HYDROCHLORIDE
• 1-BOC-3-METHYL-PIPERIDIN-4-ONE
• 1-(tert-Butoxycarbonyl)-3,3-dimethyl-4-oxopiperidine
• 1-TERT-BUTYL 3-ETHYL 3-METHYL-4-OXOPIPERIDINE-1,3-DICARBOXYLATE