Water → [(1R,3R)-3-(1H-indol-3-yl)-indan-1-yl]-methyl-amine

HRID 1435779ノート

反応式

HRID 1435779 の反応式
[CH3:1][NH:2][C@H:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[CH2:4]1.[OH-].[Na+].O>CC(C)=O.CO>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([C@H:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C@H:3]([NH:2][CH3:1])[CH2:4]2)=[CH:13]1

参加物

6

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68910845methyl-{(1R,3R)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-indan-1-yl}-amine

生成物 1

HCID 24886835[(1R,3R)-3-(1H-indol-3-yl)-indan-1-yl]-methyl-amine

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

Dimethylbromoborane (1.77 mL, 1.05 equiv) (Synthesized according to Nöth, H., Vahrenkamp, H. Journal of Organometallic Chemistry 11(1968), 399-405) was added to 3-((1R,3R)-3-azido-indan-1-yl)-1-(toluene-4-sulfonyl)-1H-indole (17.3 mmol ) in 100 mL 1,2-dichloro-ethane under argon at 0° C. The reaction mixture was warmed to room temperature and stirred 2.5 hours. 1 mL Ethanol was added. The reaction mixture was extracted with ethyl acetate and 0.5N aqueous NaOH. The organic phase was washed with brine, dried over MgSO4, concentrated in vacuo to give methyl-{(1R,3R)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-indan-1-yl}-amine after flash chromatography (ethyl acetate, methanol, triethylamine, silica gel). Methyl-{(1R,3R)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-indan-1-yl}-amine was dissolved in 8 mL acetone and 20 mL methanol. 8 mL 28% Aqueous NaOH was added and the reaction mixture was stirred in two portions at 120° C. for 10 minutes under microwave irradiation using the Emry Optimizer™ instrument. The reaction mixture was poured into 250 mL water and a precipitate was formed. Recrystallization gave 2.15 g [(1R,3R)-3-(1H-indol-3-yl)-indan-1-yl]-methyl-amine.

後処理

  1. customa precipitate was formed
  2. customRecrystallization

出典と根拠

ORDレコード
ord-9d180273c24c4058bcd68526fde0c9f7
出典データセット
uspto-grants-2009_11
特許番号
US07618967B2

反応ノート

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