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

HRID 1435779노트

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HRID 1435779 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 887Methanol용매

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온도
120 °C

실험 절차

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.

후처리

  1. customa precipitate was formed
  2. customRecrystallization

출처 및 근거

ORD 기록
ord-9d180273c24c4058bcd68526fde0c9f7
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618967B2

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