Hydrochloric Acid → Indoline

HRID 372151노트

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HRID 372151 반응식
[Sn].Cl.CO[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1OC)[NH:10][C:9](C)=[C:8]2CCN1CCN(C2C=CC=CC=2)CC1.COC1C=C2C(=CC=1OC)N[C@@H](C)[C@H]2CCN1CCN(C2C=CC=CC=2)CC1.N1C2C(=CC=CC=2)C=C1.B#B.C[O-].[Na+]>[Cr]([O-])([O-])=O.[Cu+2]>[NH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

참가 물질

9

반응물 7

HCID 313Hydrochloric AcidHCID 798IndoleHCID 4640OxypertineHCID 5352426Tin atomHCID 6328200DiboronHCID 10942334Sodium MethoxideHCID 70622462cis-5,6-Dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline

생성물 1

HCID 10328Indoline

시약·촉매·용매 1

HCID 178505374HCID 178505374, 화합물촉매

실험 절차

The tin and hydrochloric acid reduction of 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indole to cis-5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline suffers from low productivity in that it has not been possible to isolate more than 60-65% of crude product. Furthermore, this crude material is contaminated with 6-7% of trans-isomer and 1-2% of starting material. Purification by two recrystallizations is required to provide pure cis-isomer in 9% overall yield. Alternate methods of reducing the starting indole such as electrochemical-lead electrodes, diborane and sodium methoxide, and catalytic reduction with copper chromite catalyst provide from 50/50 cis/trans mixtures to 70/30 cis/trans mixtures of indoline. The stereoselectivity of the novel process of the present invention is thus completely unexpected particularly in view of the fact that ionic hydrogenation usually results in the formation of the thermodynamically more stable trans-isomer.

후처리

  1. customto isolate more than 60-65% of crude product
  2. customPurification
  3. customby two recrystallizations
  4. customto provide pure cis-isomer in 9% overall yield

출처 및 근거

ORD 기록
ord-b783020724da472eb10284fc0955e4c4
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04089853

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