Methanol → HCID 59180156, compound

HRID 601855Notes

Reaction equation

HRID 601855 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1.[OH-].[Li+].CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180126HCID 59180126, compound

Product 1

HCID 59180156HCID 59180156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-chloro-5-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.045 g, 0.15 mmol) and lithium hydroxide (0.063 g, 1.5 mmol in 2 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 mL) was used. The resulting product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane followed by reverse phase chromatography from MeOH and water (0.1% formic acid) to afford the title compound: 3.7 mg, 8.4% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.03-2.16 (m, 1H) 2.46-2.60 (m, 1H) 2.60-2.73 (m, 2H) 2.79 (dd, J=7.35, 2.03 Hz, 2H) 3.26 (m, 1H) 6.32 (s, 1H) 6.91 (dd, J=9.57, 1.51 Hz, 1H) 7.02 (dt, J=8.63, 2.13 Hz, 1H) 7.06 (s, 1H); 19F NMR δ ppm −114.32 (t, J=0.8 Hz); LCMS-MS (ESI−) 292.0 (M−H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-28128e448ed242a18ecd48d11c2fceaf
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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