Triethylamine → 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole

HRID 18236

反応式

HRID 18236 の反応式
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH:20][CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][C:9]([N:20]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[CH3:19])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 96388N-Methyl-1H-indole-3-methanamine

生成物 1

HCID 221390863-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(Benzyloxycarbonyloxy)succinimide (8.9 g, 35.7 mmole) was added to a solution of 3-(methylaminomethyl)-1H-indole (5.2 g, 32.5 mmole), from Preparation 16, and triethylamine (5.0 mL, 65.7 mmole) in DMF (100 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and the mixture was extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. Hash chromatography on silica gel (33% ethyl acetate/hexanes) gave the title compound (7.0 g, 74%) as an off-white solid: MS (ES) m/e 295 (M+H)+.

後処理

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-3bc4c41b552742a595f3a74b3cd6c1d6
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

関連ノート

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