Lithium Hydroxide → HCID 59180227, compound

HRID 601882Notes

Reaction equation

HRID 601882 reaction equation
[Cl: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>[Cl: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 59180132HCID 59180132, compound

Product 1

HCID 59180227HCID 59180227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3-chlorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.179 g, 0.65 mmol) and lithium hydroxide (0.272 g, 6.5 mmol), according to General Procedure 7. A 1:1 mixture of THF and methanol (4 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. 0.124 g. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.19 (ddt, J=12.73, 8.52, 6.46, 6.46 Hz, 1H), 2.69-2.97 (m, 3H), 4.17 (t, J=7.13 Hz, 1H), 6.53 (s, 1H), 7.11 (d, J=7.57 Hz, 1H), 7.13-7.18 (m, 2H), 7.20-7.26 (m, 1H); LCMS-MS (ESI−) 260.2 (M−H); HPLC (UV=100%), (ELSD=100%).

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-9c135a70b7be419baf71eaaa0497f283
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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