Lithium Hydroxide → HCID 59180094, compound

HRID 601853Notes

Reaction equation

HRID 601853 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[C:4]([CH3:21])[CH:3]=1.[OH-].[Li+]>CO>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[C:4]([CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59180180HCID 59180180, compound

Product 1

HCID 59180094HCID 59180094, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from methyl 4-(4-fluoro-2-methylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate and lithium hydroxide (0.92 mL, 44.2 mg, 1.85 mmol, 5.6 equiv) according to General Procedure 7. Methanol (5 mL) was used to solubilize the starting material. The resulting product was purified by silica-gel chromatography, eluting with a gradient of 0-40% EtOAc/heptane to afford to title compound. 44.9 mg. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 2.02-2.13 (m, J=12.81, 8.71, 5.64, 5.64 Hz, 1H) 2.26 (s, 3H) 2.46-2.58 (m, 1H) 2.59-2.70 (m, 1H) 2.70-2.81 (m, 3H) 3.23 (dd, J=7.47, 5.42 Hz, 1H) 6.21 (d, J=1.85 Hz, 1H) 6.87 (td, J=8.61, 2.78 Hz, 2H) 7.16 (dd, J=8.35, 6.20 Hz, 1H) 9.62 (br. s, 1H); 19F NMR (400 MHz, ACETONITRILE-d3) δ ppm −120.19 (s, 1F); LCMS-MS (ESI−) 272.31 (M−1).

Workup

  1. customThe resulting product was purified by silica-gel chromatography
  2. washeluting with a gradient of 0-40% EtOAc/heptane

Sources & evidence

ORD record
ord-2cf710eef4ee4dedabf808c3d72125de
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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