Methanol → HCID 59180118, compound

HRID 601954Notes

Reaction equation

HRID 601954 reaction equation
[Br:1][C:2]1[C:3]2[CH:13]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:4]=2[NH:5][C:6]=1[C:7]([O:9]C)=[O:8].O.[OH-].[Li+].CO>C1COCC1>[Br:1][C:2]1[C:3]2[CH:13]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:11][C:4]=2[NH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59180164HCID 59180164, compound

Product 1

HCID 59180118HCID 59180118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 3-bromo-4-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (68 mg, 0.20 mmol) and lithium hydroxide monohydrate (33 mg, 0.78 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 flash chromatography (Isco CombiFlash) eluting with a gradient of 0-80% EtOAc/Heptane to the title compound. 37 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.68-1.80 (m, 1H), 2.08-2.22 (m, 2H), 2.55-2.71 (m, 4H), 2.71-2.83 (m, 1H), 3.00-3.08 (m, 1H), 7.10-7.16 (m, 1H), 7.17-7.28 (m, 4H); LCMS-MS (ESI+) 356.0 (M+Na); HPLC (UV=93.2%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by flash chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-80% EtOAc/Heptane to the title compound

Sources & evidence

ORD record
ord-40b26dacbdee455fb3613ac9c23a3e25
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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