Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 6-propyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate
Reaction equation
O=[C:2]1[C:6]2[NH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1.[CH2:14]([Mg]Br)[CH2:15][CH3:16]>>[CH2:14]([CH:2]1[C:6]2[NH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1)[CH2:15][CH3:16]Participants
Procedure
The title compound was synthesized from methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.5 g, 2.79 mmol) and n-propylmagnesium bromide (3.5 mL, 6.97 mmol, 2.0 M in ether, 2.5 equiv) according to General Procedure 3 to give the exocyclic olefin-containing compound (E)-methyl 6-propylidene-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.96 (t, J=7.1 Hz, 3H), 1.35-1.53 (m, 3H), 1.57-1.68 (m, 1H), 1.94-2.09 (m, 1H), 2.47-2.69 (m, 3H), 2.98-3.10 (m, 1H), 3.83 (s, 3H), 6.64 (d, J=1.61 Hz, 1H), 8.69 (br. s, 1H).
Sources & evidence
- ORD record
- ord-2dbc188e793e4c158eaf8478023df65d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902252B2
Reaction notes
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