Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180229, compound

HRID 601907Notes

Reaction equation

HRID 601907 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:21]=[CH:20][C:19]([Mg]Br)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:2]2[C:6]3[NH:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:5]=3[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 57659859Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178478191HCID 178478191, compound

Product 1

HCID 59180229HCID 59180229, compound

Procedure

The title compound was synthesized in two steps. First, ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.3 g, 1.55 mmol) was reacted with 4-chlorophenyl magnesium bromide (6.2 mL, 1 M in ether, 6.2 mmol, 4 equiv) according to General Procedure 3 to give the endocyclic olefin-containing compound ethyl 6-(4-chlorophenyl)-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6, and was purified by column chromatography (Isco CombiFlash) using a 0-30% gradient (EtOAc/Heptane) over 22 minutes. 90.7 mg. LCMS m/e 312 (M+Na). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.33 (t, J=7.11 Hz, 3H), 2.27 (dddd, J=12.83, 8.60, 6.36, 6.21 Hz, 1H), 2.58-2.83 (m, 2H), 2.85-3.01 (m, J=12.81, 8.47, 8.47, 4.28 Hz, 1H), 4.27 (tt, J=7.12, 3.63 Hz, 3H), 6.73 (d, J=1.64 Hz, 1H), 7.06 (q, J=4.42 Hz, 2H), 7.28 (d, J=8.35 Hz, 2H), 8.63 (br. s, 1H).

Sources & evidence

ORD record
ord-94f710215156450f841393ae5309b2a5
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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