Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To a stirred solution of 1-tert-butoxycarbonyl-4-piperidone (10.13 g, 50.8 mmol) in anhydrous DMF (20 mL) under argon was added chlorotrimethylsilane (7.74 mL, 61.0 mmol), then anhydrous triethylamine (17.0 mL, 122 mmol) and the mixture was stirred at 80° C. for 16 h under argon. The mixture was partitioned between hexane (60 mL) and cold saturated NaHCO3 solution (50 mL). The organic layer was washed with more cold saturated NaHCO3 solution (2×30 mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 10% EtOAc/petroleum ether) to give 11.84 g (86%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 0.20 (9H, s), 1.47 (9H, s), 2.11 (2H, m), 3.52 (2H, t, J=5.8 Hz), 3.87 (2H, m), 4.80 (1H, m).
Workup
- customThe mixture was partitioned between hexane (60 mL) and cold saturated NaHCO3 solution (50 mL)
- washThe organic layer was washed with more cold saturated NaHCO3 solution (2×30 mL)
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customThe residue was purified by flash chromatography (silica gel, 10% EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-9ac35e0d601c4ea7a34f4647651f25f0
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05837715
Reaction notes
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