Methanol → HCID 59180051, compound

HRID 601866Notes

Reaction equation

HRID 601866 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)#[CH:2].[OH-].[Li+].CO>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)#[CH:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180075HCID 59180075, compound

Product 1

HCID 59180051HCID 59180051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-ethynylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.014 g, 0.050 mmol) and lithium hydroxide (0.021 g, 0.50 mmol in 0.5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (1 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: 2.8 mg, 21% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.04-2.13 (m, 1H), 2.48-2.59 (m, 1H), 2.59-2.66 (m, 2H), 2.76 (d, J=7.22 Hz, 2H), 3.22-3.29 (m, 1H), 3.41 (s, 1H), 6.30 (s, 1H), 7.18-7.22 (m, 1H), 7.25 (t, J=7.81 Hz, 1H), 7.28-7.30 (m, 1H), 7.31 (s, 1H); LCMS (ESI−) 264.2 (M−H); HPLC (UV=96.60%), (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-8146b1bcf12e4d15ab6de60493d1f25d
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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