Potassium Carbonate → tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 727088ノート

反応式

HRID 727088 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH:18]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH:16]=[C:17]([C:20]#[CH:21])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 18942192tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Potassium carbonate (1.0 g, 7.2 mmol) was added to a solution of 1-tert-butoxycarbonyl-4-trimethylsilylethynyl- 1,2,3,6-tetrahydropyridine (44.9 g, 16 lmmol) in methanol (250 ml) under a nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours. The solution was evaporated in vacuo without heating. The residue was dissolved in ether (250 ml), washed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml) before drying (MgSO4) and evaporation in vacuo to give the title compound as a white waxy solid (30.0 g, 90%); δH (CDCl3) 1.46 (9H, s, OC(CH3)3), 2.24-2.26 (2H, m, tetrahydropyridinyl CH2), 2.89 (1H, s, ethynyl CH), 3.49 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.95-3.97 (2H, m, tetrahydropyridinyl CH2) and 6.10 (1H, s, tetrahydropyridinyl CH).

後処理

  1. customThe solution was evaporated in vacuo
  2. temperaturewithout heating
  3. dissolutionThe residue was dissolved in ether (250 ml)
  4. washwashed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml)
  5. custombefore drying
  6. custom(MgSO4) and evaporation in vacuo

出典と根拠

ORDレコード
ord-e336d67b6f634052b07637b345e8cefb
出典データセット
uspto-grants-1998_01
特許番号
US05712285

反応ノート

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