Cyclopentadiene → HCID 86590323, 화합물

HRID 735275

반응식

HRID 735275 반응식
[CH3:1][CH2:2][C:3](=[O:7])[CH:4]=[CH:5][CH3:6].[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=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>[CH3:6][C@H:5]1[C@@H:10]2[CH2:11][C@H:12]([CH:8]=[CH:9]2)[C@@H:4]1[C:3](=[O:7])[CH2:2][CH3:1]

참가 물질

6

반응물 4

HCID 7612CyclopentadieneHCID 17244Hex-4-en-3-oneHCID 24247Perchloric AcidHCID 11303220(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

생성물 1

HCID 86590323HCID 86590323, 화합물수율 89%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Prepared according to general procedure A from 4-hexen-3-one (70 μL, 0.61 mmol), cyclopentadiene (75 μL, 0.91 mmol), 70% aqueous perchloric acid (10.5 μL, 0.12 mmol) and (2S, 5S)-5-Benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (30.7 mg, 0.12 mmol) in water (203 μL) for 22 hours at 0° C. Purification by silica gel chromatography (9:1 pentane:ether) provided the title compound as a colorless oil in 89% yield (88.7 mg, 0.54 mmol); 25:1 endo:exo, endo 90% ee. Product ratios were determined by GLC analysis (150° C., 23 psi); (1R, 2R, 3S, 4R) endo isomer tr=3.7 min, and (1S, 2S, 3R, 4S) endo isomer tr=3.6 min, exo isomers tr=3.4, 3.5 min. H NMR, 13C NMR, and IR data 1 were consistent with previously reported values (Zhu et al. (1997) J. Am. Chem. Soc. 119:3507-3512; Ahrendt et al. (2000) J. Am. Chem. Soc. 122:4243-4244). [α]D=+101.7 (c=1.0, CHCl3).

후처리

  1. customPrepared
  2. customPurification by silica gel chromatography (9:1 pentane:ether)

출처 및 근거

ORD 기록
ord-fdd95604a3054a2ab13da5f23d42a948
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592463B2

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