1-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate → 1-tert-Butyl 3-ethyl indoline-1,3-dicarboxylate

HRID 863298ノート

反応式

HRID 863298 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 1

HCID 539833451-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate

生成物 1

HCID 196977841-tert-Butyl 3-ethyl indoline-1,3-dicarboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 1.0 g of ethyl 1-(tert-butoxycarbonyl)indole-3-carboxylate in 20 ml of anhydrous ethanol is hydrogenated in the presence of 0.50 g of palladium-on-charcoal (5% of Pd) at 80° C. until the reaction has ended. After the reaction mixture has been filtered over Celite '545 and the filtrate has been concentrated, the oily residue is purified by means of FC over 15 g of silica gel with a 15:1 mixture of hexane and ethyl acetate as the mobile phase. This gives the title compound: Rf (G)=0.39; anal. calc. for C16H21NO4 : C65.96%, H7.27%, N4.81%; found C65.67%, H7.18%, N4.77%.

後処理

  1. filtrationAfter the reaction mixture has been filtered over Celite '545
  2. concentrationthe filtrate has been concentrated
  3. customthe oily residue is purified by means of FC over 15 g of silica gel with a 15:1 mixture of hexane and ethyl acetate as the mobile phase

出典と根拠

ORDレコード
ord-39ed7b3c3ad74147ae97dbe19d8e2b3d
出典データセット
uspto-grants-1998_02
特許番号
US05719141

反応ノート

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