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

HRID 601899Notes

Reaction equation

HRID 601899 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.[CH2:15]([Mg]Br)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:15]([CH: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)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 57659859Ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419670HCID 178419670, compound

Product 1

HCID 59180187Ethyl 6-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Procedure

The title compound was synthesized from ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.3 g, 1.55 mmol) and phenethylmagnesium bromide (7.5 mL, 0.5 M in THF, 3.7 mmol) according to General Procedure 3 to afford 96.5 mg of (E/Z)-ethyl 6-(2-phenylethylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by General Procedure 6 to give 87.3 mg of ethyl 6-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate in 90% purity. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.55 (br. s., 1H), 7.29-7.35 (m, 2H), 7.19-7.26 (m, 3H), 6.64 (d, J=1.59 Hz, 1H), 4.23-4.33 (m, 2H), 3.02-3.13 (m, 1H), 2.51-2.82 (m, 5H), 1.94-2.14 (m, 2H), 1.78-1.90 (m, 1H), 1.34 (t, J=7.13 Hz, 3H).

Sources & evidence

ORD record
ord-eb60aaf6890d4bdfa80e43f5d728d70c
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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