ChemicalBook CAS DataBase List (R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-onehydrochloride

(R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-onehydrochloride synthesis

4synthesis methods

Product Name:(R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-onehydrochloride
CAS Number:1190363-45-1
Molecular formula:C19H31NO2Si
Molecular Weight:333.54

1190363-44-0 Synthesis

(9R)-9-hydroxy-6,7,8,9-tetrahydrocyclohepta[b]pyridin-5-one

1190363-44-0
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80522-42-5 Synthesis

Triisopropylsilyl Trifluoromethanesulfonate

80522-42-5
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(R)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-onehydrochloride

1190363-45-1
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Yield:1190363-45-1 73%

Reaction Conditions:

with triethylamine in dichloromethane;benzene at 0; for 1 h;

Steps:

(R)-9-(Triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one. In a 1L round-bottomed flask was (R)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (19.14 g, 108 mmol) (azeotroped with dry benzene) in CH2Cl2 (300 mL) to give a tan solution. After cooling to 0° C., TIPS-OTf (29.3 mL, 108 mmol) and Et3N (30.1 mL, 216 mmol) were added via syringe, and the mixture was stirred at 0° C. for 1h. LCMS indicated complete conversion. Volatiles were stripped off and the residue was partitioned between NaHCO3 solution and EtOAc. The layers were separated and the organic layer was washed with brine, dried and concentrated to a tan oil (37 g). It was purified by FCC up to 20% EtOAc/hexane to afford the product as a white solid (26.3 g, 73% for two steps). MS(ESI)[M+H⁺]=334.37.

References:

US2009/258866,2009,A1 Location in patent:Page/Page column 31

39713-40-1 Synthesis