Benzonitrile, 3-(bromomethyl)- → tert-butyl (3RS,4RS)-4-[4-(3-cyano-benzyloxy)-phenyl]-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][O:16][CH:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:21][CH2:20][N:19]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:18]1.Br[CH2:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[C:42]#[N:43]>>[C:42]([C:41]1[CH:40]=[C:39]([CH:46]=[CH:45][CH:44]=1)[CH2:38][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH:22]2[CH2:21][CH2:20][N:19]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:18][CH:17]2[O:16][CH2:15][C:4]2[CH:5]=[C:6]([O:13][CH3:14])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]=2[O:2][CH3:1])=[CH:28][CH:27]=1)#[N:43]Participants
3
Reactant 2
Product 1
Procedure
In an analogous manner to that described in Example 44 e), by alkylating tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate with 3-bromomethyl-benzonitrile there was obtained tert-butyl (3RS,4RS)-4-[4-(3-cyano-benzyloxy)-phenyl]-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a beige solid; MS: 609 (M+H)+.
Sources & evidence
- ORD record
- ord-d583d0d516674897ba6f585f9cddac05
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06051712
Reaction notes
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