Ethyl Acetate → Tert-butyl 1-isopropyl-1,4-dihydrospiro[indazole-5,4'-piperidine]-1'-carboxylate

HRID 536285

반응식

HRID 536285 반응식
CN(/[CH:4]=[C:5]1/[C:6](=O)[CH:7]=[CH:8][C:9]2([CH2:22]/1)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)C.[CH:24]([NH:27][NH2:28])([CH3:26])[CH3:25].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:24]([N:27]1[C:6]2[CH:7]=[CH:8][C:9]3([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:13][CH2:14]3)[CH2:22][C:5]=2[CH:4]=[N:28]1)([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 527891-IsopropylhydrazineHCID 58252522(E)-tert-Butyl 10-((dimethylamino)methylene)-9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate

생성물 1

HCID 57337073Tert-butyl 1-isopropyl-1,4-dihydrospiro[indazole-5,4'-piperidine]-1'-carboxylate수율 98.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

(E)-tert-Butyl 10-((dimethylamino)methylene)-9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (107 g) was taken up in toluene (700 mL) and isopropyl hydrazine (44.4 g) was added. The reaction was stirred at reflux for 4 hours. The reaction was cooled to room temperature and ethyl acetate was added (500 mL). The reaction solution was washed with citric acid (2×300 mL, 10% aqueous), and water (400 mL). The organic layer concentrated in vacuo to afford tert-butyl 1-isopropyl-1,4-dihydrospiro[indazole-5,4′-piperidine]-1′-carboxylate as a yellow solid (109 g). 1H NMR (400 MHz, CDCl3) δ ppm 7.25 (s, 1H) 6.42 (dd, J=10.05, 0.49 Hz, 1H) 5.84 (d, J=9.95 Hz, 1H) 4.42-4.52 (m, 1H) 3.36-3.53 (m, 4H) 2.62 (s, 2H) 1.56-1.68 (m, 2H) 1.45-1.55 (m, 17H).

후처리

  1. temperatureat reflux for 4 hours
  2. washThe reaction solution was washed with citric acid (2×300 mL, 10% aqueous), and water (400 mL)
  3. concentrationThe organic layer concentrated in vacuo

출처 및 근거

ORD 기록
ord-6a245d9722bb43ebb5a89c0c1a313c28
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859577B2

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