(3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

81-85oC

Boiling point:

335.9±31.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.01±0.20(Predicted)

form 

Solid

color 

Pale Beige

InChI

InChI=1S/C11H19NO3/c1-11(2,3)15-10(14)12-8-5-4-6-9(13)7-8/h8H,4-7H2,1-3H3,(H,12,14)

InChIKey

VGDCXKATFLOEHF-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1CCCC(=O)C1

CAS DataBase Reference

885280-38-6

Safety Information

HS Code 

2922390090

(3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

(3-Oxocyclohexyl)carbamic Acid tert-Butyl Ester is used to prepare (benzyloxy)benzamides as TRPM8 antagonists.

Synthesis

General procedure for the synthesis of N-Boc-3-cyclohexanone amine from tert-butyl 3-hydroxycyclohexylcarbamate: To a solution of tert-butyl (3-hydroxycyclohexyl)carbamate (4.40 g, 20.46 mmol) in dichloromethane (DCM, 250 mL) was added Dess-Martin periodinane (13.0 g, 30.70 mmol). The reaction mixture was cooled in an ice bath and then stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with DCM and washed with aqueous sodium carbonate. The organic layer was separated and dried with anhydrous sodium sulfate and subsequently concentrated. The crude product was purified by silica gel column chromatography (eluent: 40% petroleum ether solution of ethyl acetate) to afford N-Boc-3-cyclohexanone amine (4.0 g, 18.78 mmol, 91% yield). Mass spectrum (ESI) m/z 214.1 [M + H]+.

References

[1] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0383
[2] Patent: WO2016/44770, 2016, A1. Location in patent: Page/Page column 736

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