Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601845Notes

Reaction equation

HRID 601845 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.[C:14]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1>>[C:14]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][C:17]([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:16][CH:15]=1

Participants

3

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419618HCID 178419618, compound

Product 1

HCID 59180167Methyl 4-(biphenyl-4-yl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (300 mg, 1.67 mmol) and biphenyl-4-ylmagnesium bromide (13.4 mL, 6.70 mmol; 0.5 M in THF) were reacted according to General Procedure 3 to give the endo olefin-containing compound methyl 4-(biphenyl-4-yl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate, which was then hydrogenated according to General Procedure 6 (with 10% Pd/C), and was purified column chromatography (Isco CombiFlash) eluting with a gradient of 0-40% EtOAc/heptane to afford the title compound. 430 mg. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.23-2.33 (m, 1H), 2.74-2.84 (m, 1H), 2.85-3.01 (m, 2H), 3.75 (s, 3H), 4.26 (t, J=7.20 Hz, 1H), 6.55 (d, J=1.76 Hz, 1H), 7.29-7.36 (m, 3H), 7.41-7.47 (m, 2H), 7.55-7.60 (m, 2H), 7.62-7.66 (m, 2H), 10.66 (s, 1H); LCMS-MS (ESI+) 340.2 (M+Na).

Sources & evidence

ORD record
ord-268b680b0ee2409ba6ab18a1c11b86d2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…