Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180127, compound

HRID 601839Notes

Reaction equation

HRID 601839 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:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>[Pd]>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178478191HCID 178478191, compound

Product 1

HCID 59180127HCID 59180127, 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 (0.3 g, 1.7 mmol) was reacted with (4-chlorophenyl)magnesium bromide (6.7 mL, IM in diethyl ether, 6.7 mmol, 4 equiv) according to General Procedure 3. The resulting endo-olefin (methyl 4-(4-chlorophenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate) was converted to the title compound by hydrogenation according to General Procedure 6 (with 5% Pd/C). The crude product was purified by preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 60% methanol and increasing to 100% over 7 minutes) afforded the title compound. 49.2 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.84 (br. s, 1H), 7.23-7.27 (m, 2H), 7.10-7.16 (m, 2H), 6.62 (d, J=1.61 Hz, 1H), 4.20 (t, J=7.22 Hz, 1H), 3.83 (s, 3H), 2.72-2.99 (m, 3H), 2.20-2.31 (m, J=12.81, 8.65, 6.47, 6.47 Hz, 1H).

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was purified by preparative HPLC
  3. customthe Chromeleon purification system
  4. temperatureincreasing to 100% over 7 minutes)

Sources & evidence

ORD record
ord-f9fa34f2a9ef409ba6263cc8e0c09e1b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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