Methanol → HCID 59180247, compound

HRID 601868Notes

Reaction equation

HRID 601868 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][CH:8]1[C:15]2[CH:14]=[C:13]([C:16]([O:18]C)=[O:17])[NH:12][C:11]=2[CH2:10][CH2:9]1)(=[O:3])[CH3:2].[OH-].[Li+].CO>C1COCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][CH:8]1[C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[NH:12][C:11]=2[CH2:10][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180064HCID 59180064, compound

Product 1

HCID 59180247HCID 59180247, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-acetylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.006 g, 0.020 mmol) and lithium hydroxide (0.010 g, 0.24 mmol in 0.5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1 mL) was used. The resulting product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-50% EtOAc/heptane affording the title compound: 0.5 mg, 9% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.56-2.61 (m, 7H), 2.79-2.91 (m, 2H), 6.29 (s, 1H), 7.39-7.44 (m, 1H), 7.44-7.46 (m, 1H), 7.78 (s, 1H), 7.82-7.86 (m, 1H); LCMS-MS (ESI−) 282.2 (M−H); HPLC (UV=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-50% EtOAc/heptane affording the title compound

Sources & evidence

ORD record
ord-4be0f54084e24007a4a2a3794eeea9bd
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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