Cyclopentadiene → HCID 91232491, compound

HRID 735285Notes

Reaction equation

HRID 735285 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:7]1[CH2:11][CH:10]=[CH:9][CH:8]=1.Cl(O)(=O)(=O)=O.C([C@@H]1N[C@H](C2OC(C)=CC=2)N(C)C1=O)C1C=CC=CC=1>O>[C@@H:9]12[CH2:10][C@H:11]([CH:7]=[CH:8]1)[C@@H:3]1[C@@H:2]2[C:1](=[O:6])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 135882-Cyclopenten-1-oneHCID 24247Perchloric AcidHCID 11303220(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

Product 1

HCID 91232491HCID 91232491, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared according to general procedure A from 2-cyclopenten-1-one (50 μL, 0.60 mmol), cyclopentadiene (74 μL, 0.90 mmol), 70% aqueous perchloric acid (10.3 μL, 0.12 mmol) and (2S, 5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (32.4 mg, 0.12 mmol) in water (150 μL) for 12 hours at 0° C. Purification by silica gel chromatography (5:1 pentane:ether) provided the title compound as a volatile white powder in 81% yield (72 mg, 0.49 mmol); 15:1 endo:exo, endo 48% ee. IR (film) 3058, 2964, 2941, 2868, 1730, 1475, 1402, 1341, 1318, 1225, 1172, 1129, 1090, 1040, 936.0, 902.3, 840.8, 804.2, 732.8 cm−1; 1H NMR (300 MHz, CDCl3) δ 6.22 (dd, J=5.7, 2.7 Hz, 1H, CH═CH), 6.11 (dd, J=5.7, 3.0 Hz, 1H, CH═CH), 3.19 (m, 1H, CHCH═CH), 3.00 (m, 1H, CHCH═CH), 2.97 (m, 1H, CHCO), 2.85 (m, 1H, C(H)HCO), 2.02 (m, 4H, CHCH2CH2, C(H)HCO, and CHCH2CH), 1.48 (m, 2H, CH2CH2CO); 13C NMR (75 MHz, CDCl 3) δ 222.6, 136.3, 135.0, 54.7, 52.6, 47.8, 47.4, 41.6, 40.9, 23.1; HRMS (CI) exact mass calc'd for (C10H12O) requires m/z 148.0888, found m/z 148.0887. [α]D+122.3 (c=1.0, CHCl3). Product ratios were determined by GLC analysis (140° C., 23 psi); (1R, 2R, 6R, 7R) endo isomer tr=7.1 min, and (1S, 2S, 6S, 7S) endo isomer tr=6.7 min, exo isomers tr=6.1 min.

Workup

  1. customPrepared
  2. customPurification by silica gel chromatography (5:1 pentane:ether)

Sources & evidence

ORD record
ord-a023e9679653459c8de6df19170b0cb9
Source dataset
uspto-grants-2009_09
Patent number
US07592463B2

Reaction notes

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