Cyclopentadiene → HCID 131726522, compound

HRID 1295197Notes

Reaction equation

HRID 1295197 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1[CH2:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH:11]2[CH:10]([CH:27]3[CH2:26][CH:25]2[CH:24]=[CH:23]3)[CH:9]1[C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7612CyclopentadieneHCID 131726523HCID 131726523, compound

Product 1

HCID 131726522HCID 131726522, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (27) (4 g; 12.2 mmol) and freshly distilled cyclopentadiene (8 mL; 12 eq.) were heated in a sealed tube in toluene for 6 h at 110° C. Concentration and purification by flash chromatography (10% EtOAc/90% hexanes) afforded 3.23 g (67%) of the desired product 28. 1H NMR (CDCl3) □.6.1 (bs, 1H), 6.0 (bs, 1H), 3.8 (dd, 1H), 3.6 (d, 1H), 3.5 (s, 1H), 3.3 (s, 1H), 3.1 (dd, 1H), 2.9 (s, 1H), 2.6 (bs, 1H), 1.6 (d, 2H), 1.5 (s, 9H), 1.3 (d, 1H), 0.9 (s, 9H), 0.15 (s, 3H), 0.1 (s, 3H)ppm.

Workup

  1. concentrationConcentration and purification by flash chromatography (10% EtOAc/90% hexanes)

Sources & evidence

ORD record
ord-bd969f836ed1410fb946868ef9e9ee20
Source dataset
uspto-grants-2007_07
Patent number
US07241796B2

Reaction notes

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