Methanol → 4-((4'-(Trifluoromethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid
Reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]3[C:23]4[CH:22]=[C:21]([C:24]([O:26]C)=[O:25])[NH:20][C:19]=4[CH2:18][CH2:17]3)[CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Li+].CO>C1COCC1>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]3[C:23]4[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[NH:20][C:19]=4[CH2:18][CH2:17]3)[CH:10]=2)=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was synthesized from methyl 4-((4′-(trifluoromethyl)biphenyl-3-yl)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.047 g, 0.12 mmol) and lithium hydroxide (0.052 g, 1.24 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound. 19.4 mg, 43% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.15 (t, J=4.73 Hz, 1H) 2.52-2.62 (m, 3H) 2.78-2.93 (m, 2H) 3.32-3.36 (m, 1H) 6.38 (s, 1H) 7.23-7.27 (m, 1H) 7.36-7.41 (m, 2H) 7.46-7.51 (m, 1H) 7.67-7.77 (m, 4H); LCMS-MS (ESI−) 384.0 (M−H); 19F NMR (376 MHz, METHANOL-d4) δ ppm −64.30 (s, 3F); HPLC (UV=99.3%), (ELSD=100%).
Workup
- customThe resulting product was purified by reverse phase HPLC
- washeluting with a gradient of 40-100% MeOH
Sources & evidence
- ORD record
- ord-8fe184bf79ce48ceb32da24856ec24a9
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902252B2
Reaction notes
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