3,5,5-Trimethyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylic acid benzyl ester → 3,5,5-Trimethyl-4-oxo-4,5,6,7-tetrahydroindole

HRID 1751974노트

반응식

HRID 1751974 반응식
C(OC([C:11]1[NH:12][C:13]2[CH2:14][CH2:15][C:16]([CH3:23])([CH3:22])[C:17](=[O:21])[C:18]=2[C:19]=1[CH3:20])=O)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:20][C:19]1[C:18]2[C:17](=[O:21])[C:16]([CH3:23])([CH3:22])[CH2:15][CH2:14][C:13]=2[NH:12][CH:11]=1

참가 물질

6

반응물 2

HCID 674199773,5,5-Trimethyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylic acid benzyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 184707113,5,5-Trimethyl-4-oxo-4,5,6,7-tetrahydroindole

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

3,5,5-trimethyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylic acid benzyl ester from the previous step, 6.60 g (21.20 mmol) and 2.0 g of 10% Pd—C was suspended in ethyl acetate 150 mL and hydrogenated under balloon of hydrogen for 3 hours. The reaction mixture was diluted with methanol 0.5 L and the mixture was stirred under Ar for 30 min to dissolve the precipitated carboxylic acid intermediate. The catalyst was then removed by filtration and the filtrates were evaporated to dryness and dried on highvac. The residue was dissolved in trifluoroacetic acid 40 mL, the solution was stirred on a 45° C. bath for 30 min, then evaporated to dryness. The residue was dried on highvac. The crude material was applied onto a column of silica (60 g) in dichloromethane and eluted with 10:1 dichloromethane-ethyl acetate mixture. Y=3.17 g (84% overall) of 3,5,5-trimethyl-4-oxo-4,5,6,7-tetrahydroindole as a white solid that gradually turns pink on air and light. 1H-NMR (d6-DMSO, 400 MHz): 10.89 (br s, 1H), 6.44 (s, 1H), 2.72 (t, 6.3 Hz, 2H), 2.12 (s, 3H), 1.85 (t, 6.3 Hz, 2H), 1.04 (s, 6H)

후처리

  1. customThe catalyst was then removed by filtration
  2. customthe filtrates were evaporated to dryness
  3. customdried on highvac
  4. dissolutionThe residue was dissolved in trifluoroacetic acid 40 mL
  5. stirringthe solution was stirred on a 45° C. bath for 30 min
  6. customevaporated to dryness
  7. customThe residue was dried on highvac
  8. washeluted with 10:1 dichloromethane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-2d3070d732ae41588f2e9091c355e441
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09162981B2

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