3-(Chloromethyl)-1-methoxynaphthalene → (3S,4R,5R)-4-[4-[3-(2-chloro-phenoxy)-propoxy]-phenyl]-3-[(4S)-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][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:17][CH:16]=2)[C@H:10]([O:33][CH2:34][C@H:35]2[CH2:39][O:38][C:37]([CH3:41])([CH3:40])[O:36]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:43][C:44]1[CH:45]=[C:46]([O:54][CH3:55])[C:47]2[C:52]([CH:53]=1)=[CH:51][CH:50]=[CH:49][CH:48]=2>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:43][C:44]2[CH:45]=[C:46]([O:54][CH3:55])[C:47]3[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:53]=2)[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:17][CH:16]=2)[C@H:10]([O:33][CH2:34][C@H:35]2[CH2:39][O:38][C:37]([CH3:41])([CH3:40])[O:36]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
In analogy to the procedure described in example 1) (f) the (3S,4R,5R)-4-[4-[3-(2-chloro-phenoxy)-propoxy]-phenyl]-3-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester was reacted with the 3-chloromethyl-1-methoxy-naphthalene [example 1) (α)] to yield the (3S,4R,5R)-4-[4-[3-(2-chloro-phenoxy)-propoxy]-phenyl]-3-[(4S)-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: 762.3 (M+H)+.
Sources & evidence
- ORD record
- ord-b2870ef139744fd1a9f47801f8ccc010
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06376672B1
Reaction notes
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