Dimethylformamide → 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 49498ノート

反応式

HRID 49498 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([CH2:26][NH2:27])[CH:24]=C.[CH3:28]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:27]([CH2:26][CH:23]=[CH2:24])[CH3:28])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 695147765-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 695147375-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester収率 85%

実験手順

8.8 g (24 mmol) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 10 ml DMF were treated with 7.11 g (100 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was concentrated in vacuo and the residue was redissolved in ether and water. 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Column chromatography with a gradient of CH2Cl2/MeOH 19:1 to 9:1 yielded 7.4 g (85%) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 361 (MH+).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was redissolved in ether
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

出典と根拠

ORDレコード
ord-0312fb6f289d413e8dd5c1f4186877a7
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

反応ノート

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