Water → HCID 59180103, compound

HRID 601880Notes

Reaction equation

HRID 601880 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19]C)=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.O.[OH-].[Li+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([OH:19])=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59180055HCID 59180055, compound

Product 1

HCID 59180103HCID 59180103, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(3,5-difluorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.081 g, 0.29 mmol) and lithium hydroxide monohydrate (61 mg, 1.45 mmol), according to General Procedure 7. A 1:6 mixture of water and methanol (MeOH)(3.5 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 the title compound 40 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.21 (ddt, 1H), 2.70-2.88 (m, 2H), 2.89-2.99 (m, 1H), 4.20 (dd, J=7.61, 6.64 Hz, 1H), 6.55 (s, 1H), 6.68-6.80 (m, 3H). 19F NMR (376 MHz, METHANOL-d4) δ ppm −112.87 (t, J=8.58 Hz). LCMS m/e 262 (M−H). 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-88efabcc6fa04028802e19444a3a98d5
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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