Water → 2-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine

HRID 1359363노트

반응식

HRID 1359363 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH:17]=[CH:16][CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=C(N2CCCC2)N=1)C1C=CC=CC=1.C[N+]1([O-])CC[O:41]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:52]>[Os](=O)(=O)(=O)=O.CC(C)=O.CC(O)(C)C>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([OH:52])[C@H:16]([OH:41])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 181822362-Benzyl-6-(3-pyrroline-1-yl)pyridineHCID 181824522-Benzyl-6-(pyrrolidine-1-yl)pyridine

생성물 1

HCID 697587312-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 6386tert-Butanol용매

실험 절차

2.3 ml of a 2-methyl-2-propanol solution containing 2.5% osmium tetraoxide was added dropwise little by little into a mixture of 11.8 g of a mixture of 2-benzyl-6-(3-pyrroline-1-yl)pyridine and 2-benzyl-6-(pyrrolidine-1-yl)pyridine, 23.5 g of aqueous 50% N-methylmorpholine-N-oxide solution, 50 ml of acetone and 10 ml of water in an ice bath. After stirring for 2 hours in an ice bath, it was further stirred at room temperature overnight. A aqueous sodium thiosulfate solution was added to the reaction solution, followed by stirring at room temperature for 30 minutes. Then, the mixture was extracted with ethyl acetate, and the organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to silica gel column chromatography and eluted with hexane/ethyl acetate (5:1) and then with ethyl acetate, to give 4.2 g of the target compound.

후처리

  1. additionwas added dropwise little by
  2. stirringit was further stirred at room temperature overnight
  3. stirringby stirring at room temperature for 30 minutes
  4. extractionThen, the mixture was extracted with ethyl acetate
  5. washthe organic phase was washed with water and brine
  6. customthe solvent was removed
  7. washeluted with hexane/ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-a30c8827e3c549c9997591e24a74bbcf
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599917B1

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