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

HRID 510522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510522
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-661773667f244dd1a7434b45065ba32b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096619B2

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