Methanol → 1-(1-(3,4-Dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidine

HRID 510522노트

반응식

HRID 510522 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][C:7]1=O.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.CO.C#N.[Na]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

8

반응물 4

HCID 887MethanolHCID 31268PyrrolidineHCID 44134943Sodium cyanohydrideHCID 574671871-(3,4-Dichlorobenzyl)-7-methoxy-3,4-dihydronaphthalen-2(1H)-one

생성물 1

HCID 574712301-(1-(3,4-Dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidine수율 25%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

1-(3,4-Dichlorobenzyl)-7-methoxy-3,4-dihydronaphthalen-2(1H)-one (5.5 g, 16.4 mmol, example 1), pyrrolidine (1.40 g, 19.7 mmol), and p-toluenesulfonic acid monohydrate (31.0 mg, 0.164 mmol) were dissolved in toluene (100 ml) and refluxed for 2 h using a Dean-Stark condenser. The solvent was removed and after addition of MeOH (50 ml) and sodium cyanohydride (1.57 g, 24.6 mmol) the mixture was stirred for 4 d at room temperature under nitrogen. Water was added, the organic phase separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were washed with saturated NaCl solution, dried over MgSO4, and concentrated to afford a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl23:97→5:95). The beige solid product (1.6 g, 25%) was obtained from precipitation in ethyl acetate/diisopropylether (1:1).

후처리

  1. temperaturerefluxed for 2 h
  2. customThe solvent was removed
  3. customthe organic phase separated
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto afford a residue that
  9. customwas purified by flash chromatography (silica gel, MeOH/CH2Cl23:97→5:95)

출처 및 근거

ORD 기록
ord-661773667f244dd1a7434b45065ba32b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096619B2

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