Water → HCID 131719973, 화합물

HRID 53868

반응식

HRID 53868 반응식
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].C([Li])CCC.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].O>C1COCC1.C(Cl)Cl.CO>[Si:27]([C:3]1([OH:4])[C:5]2[O:9][C@@H:8]3[C@@:7]45[CH2:21][CH2:20][N:18]([CH3:19])[C@@H:15]([C@@H:14]4[CH:13]=[CH:12][C@@H:10]3[OH:11])[CH2:16][C:17]([C:6]5=2)=[CH:1][CH2:2]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5288826MorphineHCID 178418339Butyllithium

생성물 1

HCID 131719973HCID 131719973, 화합물수율 56.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226129Dichloromethane methanol용매

실험 절차

To a stirred suspension of anhydrous morphine (7.01 mmol) at -78° C. in anhydrous THF (15 ml) was added 1.6M butyllithium (4.8 ml, 0.492 g, 7.68 mmol) over 8 minutes. 42 minutes later, a solution of TBDMS chloride (1.27 g, 8.43 mmol) in anhydrous THF (10 ml) was added over 10 minutes. The mixture was left to warm up gradually to room temperature overnight by which time all the material had gone into solution. Water was then added to the mixture which was extracted with dichloromethane several times. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered and the solvent removed in vacuo to leave an off-white film. Chromatography over silica using CH2Cl2 /MeOH (5:1) as eluent afforded the product as a white solid (1.58 g, 56%). Recrystallization from Et2O/petrol (boiling point 40°-60°) gave white crystalline needles (1.37 g), m.p.=120°-122° C.

후처리

  1. waitThe mixture was left
  2. extractionwas extracted with dichloromethane several times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto leave an off-white film

출처 및 근거

ORD 기록
ord-f0700bf557b44f22a9ba3a8c2632d415
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621087

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