Methanol → HCID 59180179, compound

HRID 601930Notes

Reaction equation

HRID 601930 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:10]2[NH:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][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:10]2[NH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66873680HCID 66873680, compound

Product 1

HCID 59180179HCID 59180179, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(3-chloro-5-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.055 g, 0.18 mmol) and lithium hydroxide (0.076 g, 1.8 mmol, in 2 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (4 mL) was used. The resulting product was purified by reverse phase chromatography from MeOH and water (0.1% formic acid) to afford a light brown solid: 11 mg, 21% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.97-2.17 (m, 1H) 2.30-2.53 (m, 3H) 2.69 (dd, J=13.52, 8.69 Hz, 1H) 3.09 (dd, J=13.52, 4.69 Hz, 1H) 3.33-3.40 (m, 1H) 6.56 (s, 1H) 6.85 (dd, J=9.54, 1.64 Hz, 1H) 6.94-7.07 (m, 2H); 19F NMR δ ppm −114.14 (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 reverse phase chromatography from MeOH and water (0.1% formic acid)
  2. customto afford a light brown solid

Sources & evidence

ORD record
ord-ff5cc2806b444677ba081cd3ccf75563
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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