Methanol → HCID 59180225, compound

HRID 601863Notes

Reaction equation

HRID 601863 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1.[OH-].[Li+].CO>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180059HCID 59180059, compound

Product 1

HCID 59180225HCID 59180225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3,4-dimethylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.050 g, 0.18 mmol) and lithium hydroxide (0.076 g, 1.8 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 column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane) to afford the title compound: 27 mg, 56% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.07 (ddt, J=12.40, 8.55, 6.00, 6.00 Hz, 1H), 2.16-2.29 (m, 7H), 2.45-2.73 (m, 5H), 3.22 (quin, J=6.97 Hz, 1H), 6.30 (s, 1H), 6.84-6.92 (m, 1H), 6.95 (s, 1H), 7.01 (d, J=7.61 Hz, 1H); LCMS-MS (ESI−) 268.0 (M−H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-790fd3b3edda42c7ba30f67655ebee35
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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