Water → HCID 71293338, 화합물

HRID 1479296노트

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HRID 1479296 반응식
[CH2:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CS(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=O)=O.O>CS(C)=O>[CH2:1]([N:8]1[CH2:12][C@@H:11]([O:13][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@H:10]([O:14][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 1386911-Tetradecanol, methanesulfonateHCID 7021491(3R,4R)-1-Benzylpyrrolidine-3,4-diol

생성물 1

HCID 71293338HCID 71293338, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

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온도
100 °C

실험 절차

(3R,4R)-1-Benzylpyrrolidine-3,4-diol (Diverchim S. A.; 150 mg, 0.776 mmol) was dissolved in dimethylsulfoxide (4 mL). After adding potassium hydroxide (348 mg, 6.21 mmol), the solution was stirred at 100° C. for 15 minutes. The reaction solution was further stirred at 100° C. for 4 hours after adding a dimethylsulfoxide (4 mL) solution of tetradecyl methanesulfonate (Nu-Chek Prep., Inc.; 568 mg, 1.94 mmol). The mixture was cooled to room temperature, and, after adding water, the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (chloroform 100%) to give compound VI-5 (449 mg, 98.6%).

후처리

  1. stirringThe reaction solution was further stirred at 100° C. for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationafter filtration
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform 100%)
  9. customto give compound VI-5 (449 mg, 98.6%)

출처 및 근거

ORD 기록
ord-2e14f7564599485da6a0077538701b4b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408914B2

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