3-(Chloromethyl)-1-methoxynaphthalene → (3S,4R,5R)-4-(4-allyloxy-phenyl)-3-[(S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([OH:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]=[CH2:24])=[CH:17][CH:16]=2)[C@H:10]([O:25][CH2:26][C@H:27]2[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:35][C:36]1[CH:37]=[C:38]([O:46][CH3:47])[C:39]2[C:44]([CH:45]=1)=[CH:43][CH:42]=[CH:41][CH:40]=2>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:35][C:36]2[CH:37]=[C:38]([O:46][CH3:47])[C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:45]=2)[C@@H:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]=[CH2:24])=[CH:19][CH:20]=2)[C@H:10]([O:25][CH2:26][C@H:27]2[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
In analogy to the procedure described in example 1) (f) the (3S,4R,5R)-4-(4-allyloxy-phenyl)-3-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester was reacted with 3-chloromethyl-1-methoxy-naphthalene [example 1) (α)] to yield the (3S,4R,5R)-4-(4-allyloxy-phenyl)-3-[(S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as colorless oil; MS: 634(M+H)+.
Sources & evidence
- ORD record
- ord-ec4edbb9f9984194a8d175fa0dd46fab
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06376672B1
Reaction notes
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