Methanol → HCID 59180240, compound

HRID 601865Notes

Reaction equation

HRID 601865 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=2)[CH2:7][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)[CH2:3][CH2:2]1.[OH-].[Li+].CO>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=2)[CH2:7][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)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180158HCID 59180158, compound

Product 1

HCID 59180240HCID 59180240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-cyclopropylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.020 g, 0.068 mmol) and lithium hydroxide (0.030 g, 0.71 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (2 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound: 2.2 mg, 12% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.61-0.66 (m, 2H), 0.92 (s, 2H), 1.86 (s, 1H), 2.06 (s, 1H), 2.49 (s, 1H), 2.59 (s, 2H), 2.72 (d, J=7.03 Hz, 2H), 3.23 (s, 1H), 6.30 (s, 1H), 6.84 (s, 1H), 6.96 (s, 1H), 7.12 (s, 1H); LCMS-MS (ESI−) 280.1 (M−H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH

Sources & evidence

ORD record
ord-8704f6564b7842eca3f84b1357bdf898
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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