Sodium cyanoborohydride → (3RS,4RS)-4-[8-(t-Butyldimethylsilyloxy)-1-octyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792349노트

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HRID 1792349 반응식
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1(O)[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[S:20][CH2:19][C:18]1([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH3:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>ClCCCl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[S:20][CH2:19][C:18]1([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[CH3:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 220330184-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

생성물 1

HCID 22033292(3RS,4RS)-4-[8-(t-Butyldimethylsilyloxy)-1-octyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman수율 80.4%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

4-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (14 g, 25.2 mmol) was dissolved in 1,2-dichloroethane (300 mL) and cooled to 0° C. Zinc iodide(II) (24.2 g, 75.69 mmol) and sodium cyanoborohydride (9.51 g, 151.38 mmol) was sequentially added and slowly warmed to room temperature and stirred for 2 hours. After the reaction was completed, the reaction solvent was removed under reduced pressure. The residue was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and removed by evaporation under vacuum. This product was purified by column chromatography on silica gel, eluting with 10% ethyl acetate in n-hexane. After removal of the solvent, crude 11 g of the title compound was obtained as pale yellow oil. (yield: 79.5%) Then, this compound thus obtained (11 g) was dissolved in tetrahydrofuran (300 mL). 0.2N NaHCO3(300 mL) and 10% palladium on carbon (3 g) was added and stirred for 2 day under hydrogen (atmospheric pressure). The reaction mixture was filtered through cellite and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, which was washed with water and brine. The organic solvent was dried over anhydrous magnesium sulfate and removed by evaporation under vacuum. This product was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane=1:40. After removal of the solvent, 5.6 g of the title compound was obtained as colorless oil. (yield: 50.5%).

후처리

  1. temperatureslowly warmed to room temperature
  2. customthe reaction solvent was removed under reduced pressure
  3. additionThe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customremoved by evaporation under vacuum
  7. customThis product was purified by column chromatography on silica gel
  8. washeluting with 10% ethyl acetate in n-hexane
  9. customAfter removal of the solvent

출처 및 근거

ORD 기록
ord-a8f3a55a43a74e6ba428e2e64d7b4e5d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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