Pyrrole → HCID 59180046, compound

HRID 601890Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:26][C:11]2[N:12](C(OC(C)(C)C)=O)[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:10]=2[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1CC2NC(C(OC)=O)=CC=2C1=O)C1C=CC=CC=1.N1C=CC=C1>>[CH2:1]([CH:8]1[CH2:26][C:11]2[NH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 8027Pyrrole

HCID 59180114HCID 59180114, compound

HCID 59180230HCID 59180230, compound

Product 1

HCID 59180046HCID 59180046, compoundYield 7%

Procedure

The title compound was synthesized from a mixture of 1-tert-butyl 2-methyl 5-benzyl-4-oxo-5,6-dihydrocyclopenta[b]pyrrole-1,2(4H)-dicarboxylate and methyl 5-benzyl-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.267 g, 0.99 mmol, using the formula weight of the free pyrrole) according to General Procedure 5.1. Purification by column chromatography (0-30% EtOAc/heptane) yielded methyl 5-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate as an off-white solid (0.017 g, 7% yield). Rf (1:1 EtOAc:heptane)=0.66; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.30-2.52 (m, 2H), 2.72-2.90 (m, 4H), 3.10-3.25 (m, 1H), 3.82 (s, 3H), 6.64 (s, 1H), 7.21-7.33 (m, 5H).

Workup

customPurification by column chromatography (0-30% EtOAc/heptane)

Sources & evidence

ORD record: ord-438b4a2c96e24e01be26509dd1e60961
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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