1-Phenethylamine → HCID 20244270, compound

HRID 483006Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[CH2:23][C:24]([OH:26])=O)[CH:6]=[C:7]([C:9]([CH3:17])([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=1.CC(N)C1C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:17])([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[C:5]2[C:4]=1[C:24](=[O:26])[CH2:23][CH:19]1[CH2:20][CH2:21][CH2:22][N:18]12

Participants

Reactant 2

HCID 74081-Phenethylamine

HCID 20244240HCID 20244240, compound

Product 1

HCID 20244270HCID 20244270, compound

Procedure

The dl-2-[1-[3-methoxy-5-(1,1-dimethylheptyl)-phenyl]pyrrolidin-2-yl]acetic acid provided in Example 54, Part A is resolved into dextrorotatory and levorotatory isomers via the alpha-methylbenzylamine salt by the methods of Examples 18 and 19. The resolved isomeric acids are then cyclized to provide the d- and l-isomers of 6-methoxy-8-(1,1-dimethylheptyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]quinolin-5-one. Cleavage of the methyl ether with hydrobromic acid/acetic acid by the procedure of Example 21 affords the title compounds.

Sources & evidence

ORD record: ord-432aa5f9973f464eadc9d5653ade3860
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04576964

Reaction notes

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