Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180100, compound

HRID 601908Notes

Reaction equation

HRID 601908 reaction equation
O=C1C2NC(C(OC)=O)=CC=2CC1.ClC1C=C([Mg]Br)C=CC=1.[Cl:23][C:24]1[CH:25]=[C:26]([C:30]2(O)[C:34]3[NH:35][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:37][C:33]=3[CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1>CO>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]2[C:34]3[NH:35][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:37][C:33]=3[CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 59180137Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873585HCID 66873585, compoundHCID 178478127HCID 178478127, compound

Product 1

HCID 59180100HCID 59180100, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized in two steps. First, methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.508 g, 2.84 mmol) was reacted with 3-chlorophenylmagnesium bromide (0.5 M in THF, 14 mL, 7.0 mmol) according to General Procedure 3 to give the carbinol-containing methyl 6-(3-chlorophenyl)-6-hydroxy-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 (with Pt2O), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane affording the title compound: 0.99 g (29% yield). 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.27 (ddt, J=13.17, 8.32, 5.22, 5.22 Hz, 1H), 2.58-2.67 (m, 1H), 2.72-2.79 (m, 1H), 2.90-3.01 (m, 1H), 3.73 (s, 3H), 4.31 (dd, J=8.57, 5.20 Hz, 1H), 6.63-6.65 (m, 1H), 7.06-7.10 (m, 1H), 7.13 (t, J=1.90 Hz, 1H), 7.22 (ddd, J=7.99, 2.16, 1.12 Hz, 1H), 7.30 (t, J=7.79 Hz, 1H), 10.66 (br. s, 1H); LCMS (ESI−) 274.2 (M−H).

Workup

  1. customwas purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-30% EtOAc/heptane affording the title compound

Sources & evidence

ORD record
ord-43ecda94c49444ca9ef530e351e2759d
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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