Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180160, compound

HRID 601829Notes

Reaction equation

HRID 601829 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.[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([CH2:20][Mg]Br)=[CH:16][CH:15]=1>[Pd]>[C:14]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:15]=[CH:16][C:17]([CH2:20][CH:2]2[C:9]3[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=3[CH2:4][CH2:3]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419661HCID 178419661, compound

Product 1

HCID 59180160HCID 59180160, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (200 mg, 1.12 mmol) was reacted with (biphenyl-4-ylmethyl)magnesium bromide (0.25 M in diethyl ether, 17.9 mL, 4.46 mmol) according to General Procedure 3. The resulting crude product was converted to the title compound by hydrogenation according to General Procedure 6 (with 10% Pd/C). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-40% EtOAc/heptane to afford the title compound, 122 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.08-2.19 (m, 1H), 2.51-2.72 (m, 3H), 2.75-2.87 (m, 2H), 3.26-3.35 (m, 1H), 3.76 (s, 3H), 6.34 (s, 1H), 7.24-7.28 (m, 2H), 7.28-7.33 (m, 1H), 7.38-7.44 (m, 2H), 7.51-7.56 (m, 2H), 7.59-7.63 (m, 2H); LCMS-MS (ESI+) 354.0 (M+Na).

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 0-40% EtOAc/heptane

Sources & evidence

ORD record
ord-bfd07715ac874edb83f69d59fbb87d0a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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