tert-butyl 1-(tetrahydro-2H-pyran-4-yl)piperidin-4-ylcarbamate synthesis
- Product Name:tert-butyl 1-(tetrahydro-2H-pyran-4-yl)piperidin-4-ylcarbamate
- CAS Number:873537-63-4
- Molecular formula:C15H28N2O3
- Molecular Weight:284.39
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Yield:873537-63-4 86%
Reaction Conditions:
Stage #1: Tetrahydro-4H-pyran-4-onewith acetic acid in 1,2-dichloro-ethane; for 0.5 h;
Stage #2: with sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane at 20; for 68 h;
Steps:
83
To a suspension of 9.5g (184mmol) of tert-butyl piperidin-4-yl carbamate in 200mL of 1,2-dichloroethane were added 4.4mL (47.4mmol) of tetrahydro-9H-pyran-4-one and 1.0mL of acetic acid, and the mixture was stirred for 30 minute. The reaction mixture was cooled to 0°C, and to this mixture was added 15g (71.1mmol) of sodium triacetoxyborohydride and the mixture was stirred for 4 hours at room temperature, then, 5.0g (23. 6mmol) of sodium triacetoxyborohydride was further added to the mixture and the mixture was stirred for 64 hours at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and saturated saline solution, and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 2/1) to give 11.54g (86%) of the title compound.
References:
EP1775298,2007,A1 Location in patent:Page/Page column 37
29943-42-8
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73874-95-0
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