(E)-3-[5-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic acid → (+/-)-(E)-2-(7-chloro-1'-(3-(5-fluoro-2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid

HRID 390148Notes

Reaction equation

HRID 390148 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:23]=[CH:24][C:25]([C:33]([F:36])([F:35])[F:34])=[C:26]([CH:32]=1)[CH:27]=[CH:28][C:29](O)=[O:30]>>[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:29](=[O:30])/[CH:28]=[CH:27]/[C:26]3[CH:32]=[C:22]([F:21])[CH:23]=[CH:24][C:25]=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

HCID 2737585(E)-3-[5-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic acidHCID 67224190Methyl 2-(7-chloro-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

Product 1

HCID 44226674(+/-)-(E)-2-(7-chloro-1'-(3-(5-fluoro-2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid

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 5-fluoro-2-(trifluoromethyl)cinnamic acid followed by a procedure analogous to that described in Example 2. LC-MS Method 1 tR=1.93, min, m/z=496, 498; 1H NMR (CDCl3) 1.20-1.40 (3H), 1.70 (m, 1H), 2.39 (m, 1H), 2.51 (m, 1H), 2.65-3.05 (4H), 3.36 (m, 1H), 3.62 (br s, 1H), 4.06 (d, 1H), 4.79 (d, 1H), 6.83 (d, 1H), 7.0-7.5 (5H), 7.70 (m, 1H), 7.87 (d, 1H).

Sources & evidence

ORD record
ord-4a52f6ce7a7e4f72b93005474e17f8ee
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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