Methanol → HCID 59180176, compound

HRID 601928Notes

Reaction equation

HRID 601928 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH:7]2[C:11]3[NH:12][C:13]([C:15]([O:17]CC)=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[OH-].[Na+].CO>C1COCC1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:2]=[CH:3][C:4]([CH:7]2[C:11]3[NH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59180073HCID 59180073, compound

Product 1

HCID 59180176HCID 59180176, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from ethyl 6-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.1776 g, 0.54 mmol, 1 equiv) and sodium hydroxide (1.36 mL, 13.6 mmol, 10 M, 25 equiv), according to General Procedure 7. A 4-5:1 mixture of methanol (MeOH) and THF (5-6 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 60% methanol and increasing to 100% over 7 minutes) afforded the title compound (49.3 mg, 30%) with purity by HPLC of 96.6% (UV). LCMS m/e 302.2 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.24-2.37 (m, 1H) 2.66 (ddd, J=8.74, 5.64, 5.53 Hz, 1H) 2.72-2.82 (m, 1H) 2.97 (dd, J=12.96, 4.98 Hz, 1H) 4.31 (dd, J=8.44, 5.37 Hz, 1H) 6.68 (s, 1H) 7.20 (d, J=8.20 Hz, 2H) 7.27-7.34 (m, 1H) 7.40 (t, J=7.63 Hz, 2H) 7.56 (dd, J=15.79, 7.71 Hz, 4H).

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-15bebf1200ca40d6810261bc1477c5f2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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