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

HRID 601913Notes

Reaction equation

HRID 601913 reaction equation
O=C1C2NC(C(OC)=O)=CC=2CC1.BrC1C=C(C=CC=1)C[Mg]Br.[Br:24][C:25]1[CH:26]=[C:27]([CH:42]=[CH:43][CH:44]=1)[CH2:28][C:29]1(O)[C:33]2[NH:34][C:35]([C:37]([O:39][CH3:40])=[O:38])=[CH:36][C:32]=2[CH2:31][CH2:30]1>O=[Pt]=O.CO>[Br:24][C:25]1[CH:26]=[C:27]([CH:42]=[CH:43][CH:44]=1)[CH2:28][CH:29]1[C:33]2[NH:34][C:35]([C:37]([O:39][CH3:40])=[O:38])=[CH:36][C:32]=2[CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 59180137Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873666Methyl 6-(3-bromobenzyl)-6-hydroxy-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419662HCID 178419662, compound

Product 1

HCID 59180169Methyl 6-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

The title compound was synthesized in two steps. First, methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.502 g, 1.0 mmol) was reacted with 3-bromobenzylmagnesium bromide (28 mL, 2.5 mmol) according to General Procedure 3 to give the carbinol-containing compound methyl 6-(3-bromobenzyl)-6-hydroxy-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation with PtO2 (0.045 g, 0.20 mmol) according to General Procedure 6, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane affording the title compound as a slightly yellow solid: 0.257 g (60% yield). 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.08-2.13 (m, 1H), 2.37-2.47 (m, 3H), 2.71 (dd, J1=13.47 Hz, J2=8.98 Hz, 1H), 3.19 (dd, J1=13.47 Hz, J2=4.69 Hz, 1H), 3.36-3.42 (m, 1H), 3.74 (s, 3H), 6.53 (d, J=1.9 Hz, 1H), 7.18-7.26 (m, 2H), 7.37-7.39 (m, 2H), 10.50 (s, 1H); LCMS-MS (ESI−) 332.0 (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 as a slightly yellow solid

Sources & evidence

ORD record
ord-570864e1f8d748d7bd717d4cd3377c5b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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