3-[4-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic Acid → (+/-)-(E)-2-(7-chloro-1'-(3-(4-fluoro-2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:16][C:17]([O:19]C)=[O:18].[F:21][C:22]1[CH:32]=[CH:31][C:25]([CH:26]=[CH:27][C:28](O)=[O:29])=[C:24]([C:33]([F:36])([F:35])[F:34])[CH:23]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][N:12]([C:28](=[O:29])/[CH:27]=[CH:26]/[C:25]3[CH:31]=[CH:32][C:22]([F:21])=[CH:23][C:24]=3[C:33]([F:34])([F:35])[F:36])[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:16][C:17]([OH:19])=[O:18]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared employing a procedure analogous to that described in Example 1 using methyl 2-(7-chloro-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate and 4-fluoro-2-(trifluoromethyl)cinnamic acid followed by a procedure analogous to that described in Example 2. LC-MS Method 1 tR=1.95, min, m/z=496, 498; 1H NMR (CDCl3) 1.20-1.40 (3H), 1.70 (m, 1H), 2.40 (m, 1H), 2.53 (m, 1H), 2.65-3.05 (4H), 3.30 (m, 1H), 3.62 (m, 1H), 4.06 (d, 1H), 4.79 (d, 1H), 6.80 (d, 1H), 7.1-7.5 (5H), 7.68 (m, 1H), 7.85 (d, 1H).
Sources & evidence
- ORD record
- ord-dd3df59e747a4761875c8bf76fe155a7
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383629B2
Reaction notes
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