Sodium Hydroxide → HCID 59180074, compound

HRID 601936Notes

Reaction equation

HRID 601936 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:14]3[NH:15][C:16]([C:18]([O:20]CC)=[O:19])=[CH:17][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:14]3[NH:15][C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 59180208HCID 59180208, compound

Product 1

HCID 59180074HCID 59180074, compoundYield 63%

Procedure

The title compound was synthesized from ethyl 6-(3-phenylpropyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (42.1 mg, 0.17 mmol, 1 equiv) and sodium hydroxide (0.42 mL, 10 M, 25 equiv), according to General Procedure 7. 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 (24.2 mg, 63%) with purity by HPLC of 93.1% (UV) and 97.4% (ELSD). LCMS m/z 268 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.21-7.27 (m, 2H), 7.11-7.19 (m, 3H), 6.56 (s, 1H), 2.98-3.07 (m, 1H), 2.47-2.66 (m, 5H), 1.95-2.05 (m, 1H), 1.64-1.82 (m, 3H), 1.40-1.51 (m, 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-f1ff4a34de28491e8236095b52e23aff
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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