7-[[(1,1-Dimethylethyl)dimethylsily]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinoline → alpha-(3,4-Dimethoxyphenyl)-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile
Reaction equation
ClCCCCC[C:7]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[CH:17]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:18]#[N:19].[CH3:28][C:29]([Si:32]([CH3:47])([CH3:46])[O:33][C:34]1[CH:43]=[C:42]2[C:37]([CH2:38][CH2:39][NH:40][CH2:41]2)=[CH:36][C:35]=1[O:44][CH3:45])([CH3:31])[CH3:30]>>[CH3:14][O:13][C:12]1[CH:7]=[C:8]([C:17]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:9][CH2:8][CH2:7][CH2:12][CH2:11][N:40]2[CH2:39][CH2:38][C:37]3[C:42](=[CH:43][C:34]([O:33][Si:32]([C:29]([CH3:28])([CH3:30])[CH3:31])([CH3:46])[CH3:47])=[C:35]([O:44][CH3:45])[CH:36]=3)[CH2:41]2)[C:18]#[N:19])[CH:9]=[CH:10][C:11]=1[O:15][CH3:16]Participants
3
Reactant 2
Product 1
Procedure
The procedure of Example 3 is repeated using 2.5 g of α-(5-chloropentyl-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.54 g 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinoline. This affords 1.2 g of the desired product as a light yellow oil. MS(CI): m/z 661(MH+). Calcd for C38H52N2O4SSi 1/4H2O: C=68.59, H=7.95, N=4.21, S=4.81, Si=4.22 Found C=68.73, H=7.69, N=3.99, S=4.36, Si=3.78
Sources & evidence
- ORD record
- ord-959803d74ea447c092abeeb50a338898
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561141
Reaction notes
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