Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(3-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601817Notes

Reaction equation

HRID 601817 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.[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][Mg]Cl>>[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][CH: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

Participants

3

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178478996HCID 178478996, compound

Product 1

HCID 59180250Methyl 4-(3-chlorobenzyl)-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 (447 mg, 2.5 mmol) was reacted with 3-chlorobenzylmagnesium chloride (0.25 M in hexanes, 25 mL, 6.3 mmol) according to General Procedure 3. The resulting products were then converted to the title compound by hydrogenation according to General Procedure 6 (with Pt2O). The crude product was purified by column chromatography eluting with heptane-EtOAc, gradient 0 to 40% EtOAc to afford the title compound. 262 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.04-2.15 (m, J=12.57, 8.03, 6.17, 6.17 Hz, 1H) 2.52-2.64 (m, 1H) 2.64-2.72 (m, 2H) 2.74-2.83 (m, 2H) 3.81 (s, 3H) 6.39 (d, J=1.37 Hz, 1H) 7.07 (d, J=8.25 Hz, 1H) 7.21 (d, J=1.81 Hz, 2H) 7.22-7.26 (m, 1H) 7.28-7.32 (m, 1H) 8.75 (br. s, 1H).

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was purified by column chromatography
  3. washeluting with heptane-EtOAc, gradient 0 to 40% EtOAc

Sources & evidence

ORD record
ord-42cb246bb3d3444f84d5f044316900c4
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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