1-methoxy-2-[2-[(2-methoxyphenyl)-phenylphosphoryl]ethyl-phenylphosphoryl]benzene → 3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

HRID 979373

Reaktionsgleichung

Reaktionsgleichung von HRID 979373
COC1C=CC=CC=1P(CCP(C1C=CC=CC=1)(C1C=CC=CC=1OC)=O)(C1C=CC=CC=1)=O.COC1C(P(C2C=CC=CC=2)CCP(C2C(OC)=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.[CH3:67][O:68][C:69]1[CH:70]=[C:71]([C:77]([CH:98]([CH3:100])[CH3:99])([C:96]#[N:97])[CH2:78][CH2:79][CH2:80][C:81]2[N:82]([CH3:95])[CH2:83][C:84]3[C:89]([CH:90]=2)=[CH:88][C:87]([O:91][CH3:92])=[C:86]([O:93][CH3:94])[CH:85]=3)[CH:72]=[CH:73][C:74]=1[O:75][CH3:76]>C(O)(C)C>[CH3:67][O:68][C:69]1[CH:70]=[C:71]([C:77]([CH:98]([CH3:100])[CH3:99])([C:96]#[N:97])[CH2:78][CH2:79][CH2:80][CH:81]2[CH2:90][C:89]3[C:84](=[CH:85][C:86]([O:93][CH3:94])=[C:87]([O:91][CH3:92])[CH:88]=3)[CH2:83][N:82]2[CH3:95])[CH:72]=[CH:73][C:74]=1[O:75][CH3:76]

Komponenten

5

Edukt 3

HCID 3355081-methoxy-2-[2-[(2-methoxyphenyl)-phenylphosphoryl]ethyl-phenylphosphoryl]benzeneHCID 27345571,2-Bis[(2-methoxyphenyl)phenylphosphino]ethaneHCID 20202190HCID 20202190, Verbindung

Produkt 1

HCID 1291023-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

is added to a solution of RhCl(Pφ3)3 in isopropanol at 3 atm, and the mixture heated at 50° C. for 4 hours. The product is purified to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1). Alternatively, one may hydrogenate the double bond stereoselectively using a hydrogenation catalyst with an appropriate chiral ligand, for example, 1,2-bis[P-(2-methoxyphenyl)-P-phenylphosphinyl]ethane, usually abbreviated "DiPAMP." See Knowles, Acc. Chem. Res., 6, 106-112 (1983) and the references cited therein, incorporated herein by reference in full. Thus, for example, 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2-dihydroisoquinoline (39) is added to a solution of Rh(DiPAMP)2 in isopropanol under 3 atm of H2, and the mixture heated at 50° C. for 4 hours. The product is purified to produce optically active 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1).

Aufarbeitung

  1. customThe product is purified

Quellen und Nachweise

ORD-Eintrag
ord-798a4dac3d18427d8ccf8b9cfa7f70f2
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04667038

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