Tetrahydrofuran → HCID 59180068, compound

HRID 601881Notes

Reaction equation

HRID 601881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59180127HCID 59180127, compound

Product 1

HCID 59180068HCID 59180068, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(4-chlorophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.0492 g, 0.18 mmol) and sodium hydroxide (0.45 mL, 10M, 25 equiv), according to General Procedure 7. A 1:4 mixture of THF and methanol (5 mL) was used. The resulting product was purified by preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 40% methanol and increasing to 100% over 7 minutes) afforded the title compound (22.6 mg, 48%) with purity by HPLC of 93.6% (UV) and 100% (ELSD). LCMS m/e 260 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.23-7.28 (m, 2H), 7.15-7.19 (m, 2H), 6.52 (s, 1H), 4.18 (t, J=7.17 Hz, 1H), 2.70-2.97 (m, 3H), 2.20 (dddd, J=12.75, 8.60, 6.53, 6.41 Hz, 1H).

Workup

  1. customThe resulting product was purified by preparative HPLC
  2. customthe Chromeleon purification system
  3. temperatureincreasing to 100% over 7 minutes)

Sources & evidence

ORD record
ord-dccdf5ed6ad545bb9d5fd066fc68e946
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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