Methanol → HCID 59180086, compound

HRID 601927Notes

Reaction equation

HRID 601927 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:13]3[NH:14][C:15]([C:17]([O:19]C)=[O:18])=[CH:16][C:12]=3[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Li+].CO>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:13]3[NH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:12]=3[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180077HCID 59180077, compound

Product 1

HCID 59180086HCID 59180086, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 6-(3-cyanophenyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.027 g, 0.10 mmol) and lithium hydroxide (0.044 g, 1.0 mmol in 1 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (5-6 mL) was used. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-80% MeOH: water (with 0.1% formic acid) to afford a light pink solid: 8.6 mg (34% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.21-2.30 (m, 1H) 2.65 (s, 1H) 2.76 (s, 1H) 2.93-3.03 (m, 1H) 4.33 (s, 1H) 6.68 (s, 1H) 7.40-7.44 (m, 1H) 7.44-7.49 (m, 2H) 7.54-7.58 (m, 1H); LC-MS ESI− 251.2 (m−H); HPLC (UV=97.75%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-80% MeOH
  3. customwater (with 0.1% formic acid) to afford a light pink solid

Sources & evidence

ORD record
ord-36d37f947f6846e4bf2bcc919a895a79
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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