Methanol → 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

HRID 1741419

반응식

HRID 1741419 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.[CH:13]([NH2:16])([CH3:15])[CH3:14].CO>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:13]([NH:16][CH:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)([CH3:15])[CH3:14]

참가 물질

6

반응물 3

HCID 887MethanolHCID 6363IsopropylamineHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 183672411-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-methoxy-1-indanone (0.71 g) and iso-propylamine (8 ml) in dichloromethane (10 ml) was added 1M solution of titanium(IV) chloride in dichloromethane (11 ml) at -60° C. for 15 minutes. The reaction mixture was stirred for 3 hours at the same temperature. Methanol (15 ml) was added to the reaction mixture. After being stirred for 2 hours at room temperature, the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate and 1N aqueous NaOH solution. The insoluble material was filtered off by zeolite. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene (0.89 g). MS (m/z): 206 (M+ +1) NMR (CDCl3, δ): 7.18 (1H, dd, J=7.8, 7.8 Hz), 6.97 (1H, d, J=7.8 Hz), 6.71 (1H, d, J=7.8 Hz), 4.30 (1H, t, J=6.7 Hz), 3.83 (3H, s), 3.20-2.87 (2H, m), 2.80-2.60 (1H, m), 2.50-2.35 (1H, m), 2.00-1.68 (1H, m), 1.13 (3H, d, J=6.9 Hz), 1.12 (3H, d, J=6.9 Hz)

후처리

  1. stirringAfter being stirred for 2 hours at room temperature
  2. customthe solution was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1N aqueous NaOH solution
  4. filtrationThe insoluble material was filtered off by zeolite
  5. washThe organic layer was washed with brine
  6. customThe dried solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-e3bf683236f240259165f6681f0fd040
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972965

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