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

HRID 1359363ノート

反応式

HRID 1359363 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a30c8827e3c549c9997591e24a74bbcf
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

反応ノート

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