N-[2-(4-fluoro-2-hydroxyphenyl)ethyl]acetamide → Tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-benzyloxyphenyl)piperidine-1-carboxylate

HRID 1176528Notes

Reaction equation

HRID 1176528 reaction equation
[CH2:1]([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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:42][C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][NH:51][C:52](=[O:54])[CH3:53])=[C:45](O)[CH:44]=1>>[C:52]([NH:51][CH2:50][CH2:49][C:46]1[CH:45]=[CH:44][C:43]([F:42])=[CH:48][C:47]=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][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17]1)(=[O:54])[CH3:53]

Participants

3

Reactant 2

HCID 68502030N-[2-(4-fluoro-2-hydroxyphenyl)ethyl]acetamideHCID 86610016Tert-butyl 4-(4-benzyloxyphenyl)-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate

Product 1

HCID 68499818Tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-benzyloxyphenyl)piperidine-1-carboxylate

Procedure

Analogously to Method G, 6.7 g of tert-butyl 4-(4-benzyloxyphenyl)-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate and 4.54 g of N-[2-(4-fluoro-2-hydroxyphenyl)ethyl]acetamide (Example 112b) are reacted. The title compound is obtained as a yellowish oil. Rf=0.16 (2:1 EtOAc-heptane); Rt=5.44.

Sources & evidence

ORD record
ord-1dc30964ab8742638baefafa166ee19b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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