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

HRID 49507ノート

反応式

HRID 49507 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.C([N:30]([CH2:33][CH3:34])[CH2:31]C)C.[CH2:35](CN)C=C>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:30]([CH2:33][CH:34]=[CH2:35])[CH3:31])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4437323-Buten-1-amineHCID 695152965-(5-Hydroxy-pentyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 695141225-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester収率 77.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To 2.75 g (9 mmol) 5-(5-Hydroxy-pentyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 100 ml CH2Cl2, 0.87 ml (11 mmol) methanesulfonyl chloride and 3.8 ml (27 mmol) triethylamine were added at 0° C. The solution was concentrated in vacuo to yield crude 5-(5-Methanesulfonyloxy-pentyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as yellow viscous oil, MS: 384 (MH+). The crude material was dissolved in 5 ml DMF and 5 ml (50 mmol) N-allylmethylamine. The mixture was heated to 80° C. for 3 h, concentrated and the residue was dissolved in water and ether, 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2: MeOH 9:1 yielded 2.5 g (72%) 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless liquid, MS: 359 (MH+).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customto yield crude 5-(5-Methanesulfonyloxy-pentyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as yellow viscous oil, MS
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in water
  5. additionether, 2M NaOH was added
  6. extractionthe inorganic phase was extracted with ether
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-42282892c10f496ebf0957a567f5a6e2
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

反応ノート

読み込み中…