Methanol → HCID 59180246, compound

HRID 601870Notes

Reaction equation

HRID 601870 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][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:3][CH:2]=1.O.[OH-].[Li+].CO>C1COCC1>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]=[CH:3][C:4]([CH2:7][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]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59180160HCID 59180160, compound

Product 1

HCID 59180246HCID 59180246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(biphenyl-4-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (118 mg, 0.36 mmol) and lithium hydroxide monohydrate (60 mg, 1.42 mmol in 5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (15 mL) was used. The resulting product was purified by flash chromatography (Isco CombiFlash) eluting with a gradient of 0-70% EtOAc/Heptane to give the title compound: 60 mg, 53%. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.06-2.18 (m, 1H), 2.48-2.62 (m, 1H), 2.62-2.75 (m, 2H), 2.78-2.89 (m, 2H), 3.28-3.37 (m, 1H), 6.37 (d, J=1.76 Hz, 1H), 7.29-7.37 (m, 3H), 7.41-7.48 (m, 2H), 7.57-7.63 (m, 2H), 7.63-7.69 (m, 2H), 10.38 (s, 1H); LCMS-MS (ESI−) 316.2 (M−H); HPLC (UV=99.4%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by flash chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-70% EtOAc/Heptane

Sources & evidence

ORD record
ord-b46a6bfd1cf348d594237d7e78f02d73
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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