Hydrochloric Acid → 1-cyclopentyl-1H-pyrazole

HRID 1930389ノート

反応式

HRID 1930389 の反応式
CO[CH:3](OC)[CH2:4]C(OC)OC.[CH:12]1([NH:17][NH:18][C:19](OC(C)(C)C)=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>O>[CH:12]1([N:17]2[CH:4]=[CH:3][CH:19]=[N:18]2)[CH2:13][CH2:14][CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 23113328tert-Butyl 2-Cyclopentylhydrazinecarboxylate

生成物 1

HCID 108444351-cyclopentyl-1H-pyrazole収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 1,1,3,3-tetramethoxypropane (13.6 g, 83 mmol) and N2-cyclopentyl-N1-(tert-butoxycarbonyl)hydrazine (16.6 g, 83 mmol, see Ranatunge et al., J. Med. Chem. (2004), 47, p2180-2193) in water (150 mL) was treated with cone. HCl (21 mL, 252 mmol). The resulting mixture was heated at reflux overnight. The completed reaction mixture was extracted with ether and the extracts were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo to give 1-cyclopentyl-1 H-pyrazole (8.0 g, 71% yield. 1H NMR (400 MHz, CDCl3): δ 7.52 (s, 1 H), 7.43 (s, 1 H), 6.24 (s, 1 H), 4.68 (m, 1 H), 2.20-1.71 (m, 8 H). MS (ESI) m/z; 137.1 [M+H+].

後処理

  1. additionwas treated with cone
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux overnight
  4. customThe completed reaction mixture
  5. extractionwas extracted with ether
  6. washthe extracts were washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fea1f5478c13454b9fa6f77671454262
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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