Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180126, compound

HRID 601816Notes

Reaction equation

HRID 601816 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]=[C:22]([F:24])[CH:23]=1)[CH2:18][Mg]Cl.FC1C=C(C=CC=1)/C=C1\CCC2NC(C(OC)=O)=CC\1=2>C(OCC)C.O=[Pt]=O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([F:24])[CH:23]=1)[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

6

Reactant 3

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 67269915HCID 67269915, compoundHCID 178505831HCID 178505831, compound

Product 1

HCID 59180126HCID 59180126, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 3283Diethyl EtherSolvent

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.40 g, 2.23 mmol) was reacted with 3-chloro-5-fluorobenzylmagnesium chloride ((0.25 M in diethyl ether, 23.0 mL, 5.6 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3-chloro-5-fluorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was then converted to the title compound by hydrogenation according to General Procedure 6 (with PtO2). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 0.045 g The material was taken on to hydrolysis in impure form.

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 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-d8e52292315741629bafc5389834e582
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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