Hydrochloric Acid → 1-cyclopentyl-1H-pyrazole

HRID 1930389노트

반응식

HRID 1930389 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 108444351-cyclopentyl-1H-pyrazole수율 71%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-fea1f5478c13454b9fa6f77671454262
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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