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

HRID 601883Notes

Reaction equation

HRID 601883 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([O:18]C)=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].C1COCC1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59180243Methyl 4-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801074-(3-Bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3-bromophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.315 g, 0.98 mmol) and lithium hydroxide (0.415 g, 9.9 mmol), according to General Procedure 7. A 1:1 mixture of THF and methanol (8 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. 0.119 g (40% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.16 (ddt, J=12.67, 8.50, 6.30, 6.30 Hz, 1H), 2.67-2.93 (m, 3H), 4.13 (t, J=7.20 Hz, 1H), 6.54 (s, 1H), 7.11-7.17 (m, 2H), 7.26-7.32 (m, 2H); LCMS (ESI+) 328.0 (M+Na); HPLC (UV=93.7%), (ELSD=99.9%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH

Sources & evidence

ORD record
ord-10dc9a1b108b4fc58c5496eea3a6ac32
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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