Lithium Hydroxide → HCID 59180236, compound

HRID 601878Notes

Reaction equation

HRID 601878 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[OH-].[Li+]>CO>[F:1][C:2]1[CH:3]=[C:4]([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][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59180101HCID 59180101, compound

Product 1

HCID 59180236HCID 59180236, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3-fluorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.145 g, 0.56 mmol) and lithium hydroxide (120 mg, 2.8 mmol in 1 mL water), according to General Procedure 7. In this example, methanol was used to solubilize the starting material. The resulting product was purified by chromatography over silica gel (gradient 0 to 100% EtOAc in heptane over 20 min) to give the title compound 78 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.17-2.27 (m, 1H) 2.70-2.98 (m, 3H) 4.20 (t, J=7.17 Hz, 1H) 6.54 (s, 1H) 6.85-6.92 (m, 2H) 7.01 (d, J=7.66 Hz, 1H) 7.22-7.31 (m, 1H). LCMS m/e 244 (M−H). 93% 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-306948ee1bd54a91a21b938567f0326a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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