N-(2-hydroxyphenethyl)acetamide → tert-Butyl 3-{2-[2-(2-acetylaminoethyl)phenoxy]ethoxy}-4-(4-methoxyphenyl)piperidine-1-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]2[O:22][CH2:23][CH2:24][O:25]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1.O[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][CH2:44][NH:45][C:46](=[O:48])[CH3:47]>>[C:46]([NH:45][CH2:44][CH2:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[O:25][CH2:24][CH2:23][O:22][CH:10]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:11]1)(=[O:48])[CH3:47]Participants
3
Procedure
Analogously to Method G, 0.24 g of tert-butyl 4-(4-methoxyphenyl)-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate and 0.17 g of N-[2-(2-hydroxyphenyl)ethyl]acetamide are reacted. The title compound is obtained as an orange oil. Rf=0.50 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.85.
Sources & evidence
- ORD record
- ord-5bffab5d09994fd0ad03bfbbc6b7fbec
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
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