Methanol → HCID 59180063, compound

HRID 601861Notes

Reaction equation

HRID 601861 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1.[OH-].[Li+].CO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180231HCID 59180231, compound

Product 1

HCID 59180063HCID 59180063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3,4-dimethoxybenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.050 g, 0.16 mmol) and lithium hydroxide (0.067 g, 1.6 mmol in 3 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane) to afford the title compound: 11 mg, 23% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.06-2.18 (m, 1H), 2.50-2.68 (m, 3H), 2.68-2.81 (m, 2H), 3.20-3.35 (m, 1H), 3.77 (s, 3H), 3.81 (s, 3H), 6.35 (s, 1H), 6.72 (m, 2H), 6.86 (d, J=8.0 Hz, 1H); LCMS-MS (ESI−) 300.0 (M−H); HPLC (UV=96%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-ec66ce706cd54774aaea388636eb4ead
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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