ChemicalBook CAS DataBase List (3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER

(3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER synthesis

5synthesis methods

Product Name:(3-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER
CAS Number:885280-38-6
Molecular formula:C11H19NO3
Molecular Weight:213.27

(3-HYDROXY-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER

610302-03-9

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

885280-38-6

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]+.

610302-03-9 Synthesis

610302-03-9
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$30.00/250mg

885280-38-6
176 suppliers
$8.00/250mg

Yield:885280-38-6 91%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 2 h;Cooling with ice;

Steps:

27.D tert-butyl(3-oxocyclohexyl)carbamate
D.
tert-butyl(3-Oxocyclohexyl)carbamate
To a solution of tert-butyl (3-hydroxycyclohexyl)carbamate (4.40 g, 20.46 mmol) in DCM (250 mL) was added Dess-Martin periodinane (13.0 g, 30.70 mmol) in portions under cooling in an ice bath.
The mixture was stirred at room temperature for 2 h.
The reaction was diluted with DCM and washed with aqueous sodium carbonate.
The separated organic layer was dried over anhydrous sodium sulfate and concentrated.
The crude compound was purified by silica gel column chromatography (40% ethyl acetate in petroleum ether) to afford the title compound (4.0 g, 18.78 mmol, 91% yield). MS (ESI) m/z 214.1 [M+H]⁺.

References:

Papa, Patrick;Cathers, Brian Edwin;CALABRESE, Andrew Antony;WHITEFIELD, Brandon Wade;BENNETT, Brydon;CASHION, Daniel;MORTENSEN, Deborah;HUANG, Dehua;TORRES, Eduardo;PARNES, Jason;SAPIENZA, John;HANSEN, Joshua;LEFTHERIS, Katerina;CORREA, Matthew;DELGADO, Maria Mercedes;RAHEJA, Neil;BAHMANYAR, Sami;HEGDE, Sayee;NORRIS, Stephen;PLANTEVIN-KRENITSKY, Veronique US2015/175557, 2015, A1 Location in patent:Paragraph 0383

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