Reaktionsgleichung
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=O)[CH:2]=1.[NH2:18][N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][O:25][CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:26][O:25][CH2:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[N:18]=[C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of (±)-2-(3-quinolinyl)cyclohexanone (0.5 g, 2.2 mmol), (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (`SAMP`)(0.28 g, 2.2 mmol) and p-toluenesulphonic acid (10 mg) was refluxed in toluene (15 ml) for 2.5 hours. The toluene was removed in vacuo (40° C./14 mmHg,) to give a crude oil which was partitioned between water (20 ml) and ethyl acetate (25 ml). The aqueous layer was extracted with ethyl acetate (2×25 ml) and the combined organic extracts were dried over sodium sulphate then concentrated in vacuo to give (2S)-(+)-2-(methoxymethyl) -1-[2-(3-quinolinyl)cyclohexylideneamino]pyrrolidine and (2S)-(-)-2-(methoxymethyl)-1-[2-(3-quinolinyl)cyclohexylideneamino]pyrrolidine as a 50:50 mixture of diastereoisomers (0.69 g, 2 mmol).
Aufarbeitung
- customThe toluene was removed in vacuo (40° C./14 mmHg,)
- customto give a crude oil which
- customwas partitioned between water (20 ml) and ethyl acetate (25 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (2×25 ml)
- dry with materialthe combined organic extracts were dried over sodium sulphate
- concentrationthen concentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-bab73a4a228c43358d83afa5f35ad8c6
- Quelldatensatz
- uspto-grants-1992_09
- Patentnummer
- US05151436
Verknüpfte Notizen
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