Methanol → 6-(3-Bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601925Notes

Reaction equation

HRID 601925 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:12]3[NH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].CO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:12]3[NH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180226Methyl 6-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801506-(3-Bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.213 g, 0.67 mmol) and lithium hydroxide (0.281 g, 6.70 mmol in 4 mL water), according to General Procedure 7. A 1:2 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford a light pink solid: 0.098 g (48% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.23 (ddt, J=13.14, 8.21, 5.27, 5.27 Hz, 1H), 2.62 (ddd, J=14.31, 8.65, 5.34 Hz, 1H), 2.69-2.78 (m, 1H), 2.87-2.98 (m, 1H), 4.24 (dd, J=8.40, 5.17 Hz, 1H), 6.67 (s, 1H), 7.07 (d, J=7.61 Hz, 1H), 7.18 (t, J=7.81 Hz, 1H), 7.25 (s, 1H), 7.33 (d, J=7.86 Hz, 1H); LCMS (ESI+) 306.0 (M+H); HPLC (UV=96.1%), (ELSD=99.3%).

Workup

  1. customThe resulting product was purified reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH
  3. customwater (with 0.1% formic acid) to afford a light pink solid

Sources & evidence

ORD record
ord-67fd2e301d224f4191f6f81fc607e097
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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