ChemicalBook CAS DataBase List CarbaMic acid, N-[(1S)-1-(aMinoMethyl)-2-[(3R)-tetrahydro-2H-pyran-3-yl]ethyl]-N-Methyl-, 1,1-diMethylethyl ester

CarbaMic acid, N-[(1S)-1-(aMinoMethyl)-2-[(3R)-tetrahydro-2H-pyran-3-yl]ethyl]-N-Methyl-, 1,1-diMethylethyl ester synthesis

13synthesis methods

Product Name:CarbaMic acid, N-[(1S)-1-(aMinoMethyl)-2-[(3R)-tetrahydro-2H-pyran-3-yl]ethyl]-N-Methyl-, 1,1-diMethylethyl ester
CAS Number:942145-27-9
Molecular formula:C14H28N2O3
Molecular Weight:272.38

Carbamic acid, N-methyl-N-[(1S)-1-[[[(phenylmethoxy)carbonyl]amino]methyl]-2-[(3R)-tetrahydro-2H-pyran-3-yl]ethyl]-, 1,1-dimethylethyl ester

1093865-03-2
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CarbaMic acid, N-[(1S)-1-(aMinoMethyl)-2-[(3R)-tetrahydro-2H-pyran-3-yl]ethyl]-N-Methyl-, 1,1-diMethylethyl ester

942145-27-9
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Yield:942145-27-9 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20; for 1.5 h;Inert atmosphere;

Steps:

6

INTERMEDIATE PREPARATION 6; 1,1 -Dimethylethyl {(15)-2-amino-l-[(3Λ)-tetrahydro-2/7-pyran-3- ylmethyl]ethyl}methylcarbamate; To a flask containing the 1,1 -dimethylethyl methyl {(15)-2- ({[(phenylmethyl)oxy]carbonyl}amino)-l-[(3/?)-tetrahydro-2//-pyran-3- ylmethyl]ethyl}carbamate and a large stirbar was added MeOH (10 mL). Palladium on carbon (0.093 g, 10% on carbon, 5 mol%) was added and a balloon of hydrogen affixed to the flask with a three-way valve. Very carefully, the contents of the flask were partially evacuated and refilled with N₂ several times while stirring, then partially evacuated and refilled with H₂ several times in such a way as to avoid bumping or excessive boiling. The hydrogenation was allowed to proceed at rt with vigorous stirring. After 1.5 h, TLC (5% MeOH/DCM) showed that the reaction was complete. The mixture was filtered through a pad of Celite and sand (cloudy, colorless), then through a 0.45 micron PTFE syringe filter (clear, colorless), and evaporated to yield 473.2 mg of 1 ,1 -dimethylethyl {(15)-2-amino-l-[(3/?)-tetrahydro-2H-pyran-3- ylmethyl]ethyl}methylcarbamate as a clear slightly rose-colored heavy oil after drying in vacuo (100%).

References:

WO2009/154766,2009,A1 Location in patent:Page/Page column 47