Methanol → HCID 59180091, compound

HRID 601887Notes

Reaction equation

HRID 601887 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:21]3[CH:20]=[C:19]([C:22]([O:24]C)=[O:23])[NH:18][C:17]=3[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].CO>C1COCC1>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:21]3[CH:20]=[C:19]([C:22]([OH:24])=[O:23])[NH:18][C:17]=3[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59180218HCID 59180218, compound

Product 1

HCID 59180091HCID 59180091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(4-benzylphenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (150 mg, 0.45 mmol) and lithium hydroxide monohydrate (108 mg, 4.5 mmol), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (10 mL) was used. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to give a pure product (50 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.14-2.25 (m, 1H), 2.66-2.94 (m, 3H), 3.91 (s, 2H), 4.14 (t, J=7.30 Hz, 1H), 6.51 (s, 1H), 7.09 (s, 5H), 7.12-7.19 (m, 3H), 7.21-7.28 (m, 2H). LCMS m/e 316 (M−H) and 100% pure by HPLC.

Workup

  1. customThe resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min)

Sources & evidence

ORD record
ord-b68dfddc53c24be4b1d09ba63b61ec30
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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