Methanol → HCID 59180112, compound

HRID 601934Notes

Reaction equation

HRID 601934 reaction equation
[C:1]1([CH2:11][CH2:12][CH:13]2[C:17]3[NH:18][C:19]([C:21]([O:23]C)=[O:22])=[CH:20][C:16]=3[CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].CO>C1COCC1>[C:1]1([CH2:11][CH2:12][CH:13]2[C:17]3[NH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][C:16]=3[CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180182HCID 59180182, compound

Product 1

HCID 59180112HCID 59180112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(2-(naphthalen-1-yl)ethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.051 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 0-60% EtOAc/heptane. 17 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.85 (dq, J=13.45, 7.90 Hz, 1H) 2.08-2.27 (m, 2H) 2.46-2.62 (m, 1H) 2.62-2.80 (m, 2H) 3.04-3.22 (m, 3H) 6.61 (s, 1H) 7.29-7.41 (m, 2H) 7.41-7.54 (m, 2H) 7.64-7.73 (m, 1H) 7.80-7.87 (m, 1H) 8.03 (d, J=8.35 Hz, 1H); LCMS-MS (ESI−) 304.0 (M−H); HPLC (UV=95.2%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-60% EtOAc/heptane

Sources & evidence

ORD record
ord-5d7d0aa629e2449d99bf165faaeb6468
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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