HCID 57659876, compound → HCID 59180208, compound

HRID 601917Notes

Reaction equation

HRID 601917 reaction equation
O=[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1.[C:15]1([CH2:21][CH2:22][CH2:23][Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([CH2:21][CH2:22][CH2:23][CH:4]2[C:5]3[NH:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:9]=3[CH2:2][CH2:3]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 57659876HCID 57659876, compoundHCID 178418471HCID 178418471, compound

Product 1

HCID 59180208HCID 59180208, compound

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).

Sources & evidence

ORD record
ord-b67d8d8f95d2491daab716d8f7d4e7a5
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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