Benzoyl Peroxide → Glycine, N-methyl-, ethyl ester

HRID 619692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619692
[OH:1][C:2]1[C:18]([OH:19])=[CH:17][CH:16]=[C:15]2[C:3]=1[CH2:4][C:5]1[C:6]3[CH:7]2[CH2:8][NH:9][CH2:10][C:11]=3[CH:12]=[CH:13][CH:14]=1.C1NCC2=CC=CC3=C2[C@@H]1C1C=C[C:34]([OH:37])=[C:33](O)C=1C3.C[N:40]1[CH2:49][C:48](=[O:50])C2C(=CC=CC=2)[CH2:41]1.C(OC(C1C(C)=CC=CC=1)=O)C.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[CH2:8]1[NH:9][CH2:10][C:11]2=[CH:12][CH:13]=[CH:14][C:5]3=[C:6]2[C@@H:7]1[C:15]1[CH:16]=[CH:17][C:18]([OH:19])=[C:2]([OH:1])[C:3]=1[CH2:4]3.[CH2:34]([O:37][C:48](=[O:50])[CH2:49][NH:40][CH3:41])[CH3:33]

Komponenten

8

Edukt 6

HCID 7187Benzoyl PeroxideHCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimideHCID 52494902,3,7,11b-Tetrahydro-1H-dibenzo[de,h]isoquinoline-8,9-diolHCID 9816455DinapsolineHCID 106308122-Methyl-2,3-dihydroisoquinolin-4(1H)-one

Produkt 2

HCID 95849Glycine, N-methyl-, ethyl esterHCID 9816455Dinapsoline

Versuchsvorschrift

One compound provided in accordance with the present invention is (±)-8,9-dihydroxy-2,3,7,11b-tetrahydro-1H-naphtho[1,2,3-de]isoquinoline denominated hereinafter as "dinapsoline." Dinapsoline is synthesized from 2-methyl-2,3-dihydro-4(1H)-isoquinolone according to the procedure depicted generally in FIGS. 1 and 2. Side chain bromination of ethyl-o-toluate (5a) with NBS in the presence of benzoyl peroxide produced compound 5b. Alkylation of sarcosine ethyl ester with compound 5b afforded compound 6, which after Dieckmann condensation and subsequent decarboxylation on acidic hydrolysis yielded compound 7.

Aufarbeitung

  1. customOne compound provided in accordance with the present invention

Quellen und Nachweise

ORD-Eintrag
ord-ab540c985d21479987a340ddcd8d8d53
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959110

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