Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate
Reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Si:15](Cl)([CH3:18])([CH3:17])[CH3:16].CCN(CC)CC>CN(C=O)C>[CH3:16][Si:15]([CH3:18])([CH3:17])[O:1][C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:7]=1Participants
5
Conditions
- Temperature
- 70 °C
Procedure
To a 1.0 L flask was added tert-butyl 4-oxopiperidine-1-carboxylate (150.0 g, 752.8 mmol), which was dissolved in DMF (400 mL). To this solution was added TMS-Cl (114.7 mL, 903.4 mmol), followed by NEt3 (251.8 mL, 1807 mmol). The resulting heterogeneous mixture was warmed to 70° C. and stirred overnight under a N2 atmosphere. The mixture was cooled to ambient temperature, diluted with hexanes (250 mL) and filtered. The solids were washed with hexanes (4×250 mL). The combined organic phases were washed with a saturated aqueous NaHCO3 (3×250 mL) and brine (3×250 mL), dried over Na2SO4, and concentrated. The crude product was carried on directly to the next step.
Workup
- temperatureThe mixture was cooled to ambient temperature
- filtrationfiltered
- washThe solids were washed with hexanes (4×250 mL)
- washThe combined organic phases were washed with a saturated aqueous NaHCO3 (3×250 mL) and brine (3×250 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-45cdb7273dda4497b411075e02a3222c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557809B2
Reaction notes
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