Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180198, compound

HRID 601818Notes

Reaction equation

HRID 601818 reaction equation
O=[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:18][Mg]Cl.ClC1C=C(C=C(F)C=1)/C=C1\CCC2NC(C(OC)=O)=CC\1=2>>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:18][CH:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873713HCID 66873713, compoundHCID 178478999HCID 178478999, compound

Product 1

HCID 59180198HCID 59180198, compound

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.50 g, 2.8 mmol) was reacted with 3,4-dichlorobenzylmagnesium chloride (0.25 M in diethyl ether, 28.0 mL, 7.0 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3,4-dichlorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was then converted to the title compound by hydrogenation according to General Procedure 6 (with 5% Pt2O). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-50% EtOAc/heptane to afford the title compound. 0.064 g.

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was purified by column chromatography (Isco CombiFlash)
  3. washeluting with a gradient of 0-50% EtOAc/heptane

Sources & evidence

ORD record
ord-1c293f8060c3404286fe77fc2d020639
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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