Methanol → HCID 59180219, compound

HRID 601888Notes

Reaction equation

HRID 601888 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][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:4][CH:3]=1.[OH-].[Li+].CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][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:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180083HCID 59180083, compound

Product 1

HCID 59180219HCID 59180219, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(4-chlorobenzylamino)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.023 g, 0.075 mmol) and lithium hydroxide (0.023 g, 0.55 mmol in 3 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by reverse phase chromatography, eluting with MeOH in water (0.1% formic acid) a to afford a yellow solid: 3 mg, 14% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.47-2.58 (m, 1H), 2.71-2.83 (m, 1H), 2.87-3.06 (m, 2H), 4.23 (q, J=13.16 Hz, 2H), 4.54-4.67 (m, 1H), 6.81 (s, 1H), 7.38-7.56 (m, 4H), 8.49 (s, 1H); LCMS-MS (ESI−) 289.0 (M−H).

Workup

  1. customThe resulting product was purified by reverse phase chromatography
  2. washeluting with MeOH in water (0.1% formic acid)
  3. customa to afford a yellow solid

Sources & evidence

ORD record
ord-4030c18a1fef4065bc3ddeb5a3310efb
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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