Boc-6-amino-1,2,3,4-tetrahydroquinoline → tert-Butyl N-[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]carbamate

HRID 585378Notes

Reaction equation

HRID 585378 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11](O)[CH2:10][C@@H:9]1[CH3:19])=[O:7].[NH:25]1[C:34]2[C:29](=[CH:30][C:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:25]2[C:34]3[C:29](=[CH:30][C:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)[CH2:10][CH:9]1[CH3:19])=[O:7]

Participants

3

Reactant 2

HCID 4083416Boc-6-amino-1,2,3,4-tetrahydroquinolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 22339238tert-Butyl N-[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]carbamateYield 13%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (712 mg, 2.18 mmol) prepared in Reference Example 1 and tert-butyl N-(1,2,3,4-tetrahydro-6-quinolinyl)carbamate (1.35 g, 5.44 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (157 mg, yield: 13%) as a white crystal. (cis:trans=4.8:1)

Sources & evidence

ORD record
ord-baf94d6fb3e4406aa0049a646014e86a
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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