Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 356677ノート

反応式

HRID 356677 の反応式
[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]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

生成物 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  1. customThe mixture was partitioned between hexane (60 mL) and cold saturated NaHCO3 solution (50 mL)
  2. washThe organic layer was washed with more cold saturated NaHCO3 solution (2×30 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 10% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-9ac35e0d601c4ea7a34f4647651f25f0
出典データセット
uspto-grants-1998_11
特許番号
US05837715

反応ノート

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