2,6-Lutidine → (3R,4R,5S)-5-methyl-3-phenethyl-4-((triisopropyl-silyl)oxy)dihydrofuran-2(3H)-one

HRID 58953노트

반응식

HRID 58953 반응식
[OH:1][C@H:2]1[C@H:6]([CH3:7])[O:5][C:4](=[O:8])[C@@H:3]1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C=CC=C(C)N=1.FC(F)(F)S(O[Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:7][C@@H:6]1[O:5][C:4](=[O:8])[C@H:3]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:2]1[O:1][Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33]

참가 물질

6

반응물 4

HCID 79372,6-LutidineHCID 516892Sodium BicarbonateHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 117974545(3R,4R,5S)-4-hydroxy-5-methyl-3-phenethyldihydrofuran-2(3H)-one

생성물 1

HCID 123299646(3R,4R,5S)-5-methyl-3-phenethyl-4-((triisopropyl-silyl)oxy)dihydrofuran-2(3H)-one수율 59.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3R,4R,5S)-4-hydroxy-5-methyl-3-phenethyldihydrofuran-2(3H)-one (800 mg, 3.63 mmol) in CH2Cl2 (20 mL) were added 2,6-dimethylpyridine (592 μl, 5.08 mmol) and triisopropylsilyl trifluoromethanesulfonate (1171 μL, 4.36 mmol) at 0° C., and the mixture was warmed to room temperature while stirring overnight. The reaction mixture was poured onto 50 mL saturated sodium bicarbonate solution and mixed thoroughly. The phases were separated, and the aqueous extracted with CH2Cl2 (2×25 mL). The combined CH2Cl2 extracts were dried and concentrated to a colorless oil which was purified by flash chromatography (SiO2, 0→50% EtOAc/hexanes) to give (3R,4R,5S)-5-methyl-3-phenethyl-4-((triisopropylsilyl)oxy)dihydro-furan-2(3H)-one (809 mg, 53%): 1H NMR (400 MHz, CDCl3) δ 7.33-7.25 (m, 2H), 7.25-7.17 (m, 3H), 3.98 (dd, J=5.9, 4.8 Hz, 1H), 4.34-4.24 (m, 1H), 2.99-2.88 (m, 1H), 2.88-2.76 (m, 1H), 2.61-2.51 (m, 1H), 2.04-1.94 (m, 2H), 1.43 (d, J=6.5 Hz, 3H), 1.09-0.99 (m, 21H); 13C NMR (101 MHz, CDCl3) δ 176.64, 140.98, 128.57, 128.51, 126.16, 82.10, 79.45, 49.17, 32.96, 31.14, 19.10, 18.00, 17.71; ESIMS m/z 378 ([M+H]+).

후처리

  1. additionmixed thoroughly
  2. customThe phases were separated
  3. extractionthe aqueous extracted with CH2Cl2 (2×25 mL)
  4. dry with materialThe combined CH2Cl2 extracts were dried
  5. concentrationconcentrated to a colorless oil which
  6. customwas purified by flash chromatography (SiO2, 0→50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-5927ef077ffa469daf0c8d4bc94ff615
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439422B2

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