N-[2-(4-fluoro-2-hydroxyphenyl)ethyl]acetamide → tert-Butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-{4-[3-(2-chlorophenoxy)propoxy]phenyl}piperidine-1-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:45]=[CH:44][CH:43]=[CH:42][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]2[O:28][CH2:29][CH2:30][O:31]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:11][CH:10]=1.[F:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH:55][C:56](=[O:58])[CH3:57])=[C:49](O)[CH:48]=1>>[C:56]([NH:55][CH2:54][CH2:53][C:50]1[CH:49]=[CH:48][C:47]([F:46])=[CH:52][C:51]=1[O:31][CH2:30][CH2:29][O:28][CH:16]1[CH:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]3[CH:42]=[CH:43][CH:44]=[CH:45][C:2]=3[Cl:1])=[CH:10][CH:11]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17]1)(=[O:58])[CH3:57]Participants
3
Reactant 2
Product 1
Procedure
Analogously to Method G, 0.28 g of tert-butyl 4-{4-[3-(2-chlorophenoxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate and 0.17 g of N-[2-(4-fluoro-2-hydroxyphenyl)ethyl]acetamide (Example 112b) are reacted. The title compound is obtained as a yellow oil. Rf=0.58 (EtOAc); Rt=5.74.
Sources & evidence
- ORD record
- ord-e29b448096c94b88bf9ef333960c8df2
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
Loading…