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 1751974ノート

反応式

HRID 1751974 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-2d3070d732ae41588f2e9091c355e441
出典データセット
uspto-grants-2015_10
特許番号
US09162981B2

反応ノート

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