HCID 86638800, compound → HCID 59180208, compound

HRID 601918Notes

Reaction equation

HRID 601918 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[C:10]2\[CH2:11][CH2:12][C:13]3[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][C:14]\2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:14]3[NH:15][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:17][C:13]=3[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 86638800HCID 86638800, compound

Product 1

HCID 59180208HCID 59180208, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was synthesized from ethyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.3 g, 1.55 mmol, 1 equiv) and 3-phenyl-propyl magnesium bromide (12.4 mL, 0.5M in THF, 6.2 mmol, 4 equiv) according to General Procedure 3 to give the exo olefin-containing compound (E)-ethyl 6-(3-phenylpropylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 with 5% Pd on carbon, and 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 (42.1 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.67 (br. s., 1H), 7.28-7.33 (m, 2H), 7.16-7.23 (m, 3H), 6.64 (d, J=1.64 Hz, 1H), 4.25-4.34 (m, 2H), 3.00-3.09 (m, 1H), 2.51-2.68 (m, 5H), 1.97-2.07 (m, 1H), 1.65-1.77 (m, 3H), 1.47-1.55 (m, 1H), 1.34 (t, J=7.13 Hz, 3H).

Workup

  1. customwas purified by preparative HPLC
  2. customthe Chromeleon purification system
  3. temperatureincreasing to 100% over 7 minutes)

Sources & evidence

ORD record
ord-a1690b8f160b4af6ba869cdab192982f
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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