Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180228, compound

HRID 601912Notes

Reaction equation

HRID 601912 reaction equation
O=[C:2]1[C:6]2[NH:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:19][Mg]Cl>>[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:19][CH:2]1[C:6]2[NH:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 57659859Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178505831HCID 178505831, compound

Product 1

HCID 59180228HCID 59180228, compoundYield 11%

Procedure

The title compound was synthesized in two steps. Ethyl 6-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 to give the exocyclic olefin-containing compound (Z)-ethyl 6-(3-chloro-5-fluorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 (with Pt2O), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-20% EtOAc/heptane affording the product as brown solid: 0.055 g (11% yield).

Sources & evidence

ORD record
ord-b3b4f1a4e05a4a1793b371e651ae1086
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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