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

HRID 636545Notes

Reaction equation

HRID 636545 reaction equation
[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]

Participants

8

Reactant 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

Product 2

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

Procedure

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.

Workup

  1. customOne compound provided in accordance with the present invention

Sources & evidence

ORD record
ord-20c0db3282de49a1a45ad3080f2e2a79
Source dataset
uspto-grants-2001_02
Patent number
US06194423B1

Reaction notes

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