Tetrahydrofuran → N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-3-oxopropan-1-amine hydrochloride

HRID 657556Notes

Reaction equation

HRID 657556 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([CH2:14][N:15](C)[CH2:16][CH2:17][C:18]([N:20]1[CH2:26][CH2:25][C:24]3[CH:27]=[C:28]([O:33][CH3:34])[C:29]([O:31][CH3:32])=[CH:30][C:23]=3[CH2:22][CH2:21]1)=[O:19])[CH2:7]2.COC1C=C2C(=CC=1OC)[C@@H](CN)C2.C1COCC1>O1CCOCC1>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C@@H:8]([CH2:14][NH:15][CH2:16][CH2:17][C:18]([N:20]1[CH2:21][CH2:22][C:23]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:24]=3[CH2:25][CH2:26]1)=[O:19])[CH2:7]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 115066164,5-Dimethoxy-1-(aminomethyl)benzocyclobutane, (S)-HCID 68972400N-[(3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl]-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-N-methyl-3-oxopropan-1amine hydrochloride

Product 1

HCID 68974197N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-3-oxopropan-1-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Obtained in the same manner as the product of Example 1, but with replacement of the racemic [(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl]methylamine in Step 4 by {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine and of the THF by dioxane.

Sources & evidence

ORD record
ord-e2871126c6ee4953917bd777abdded10
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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