2,2-Dimethoxypropane → 2-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine

HRID 1359368ノート

反応式

HRID 1359368 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([OH:19])[C@H:16]([OH:20])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1(C)[C@]2(CS(O)(=O)=O)C(C[C@H:23]1CC2)=O.COC(OC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:15][C@H:16]3[O:20][C:22]([CH3:23])([CH3:21])[O:19][C@H:17]3[CH2:18]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 64952,2-DimethoxypropaneHCID 65617D-Camphorsulfonic AcidHCID 516892Sodium BicarbonateHCID 697587312-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine

生成物 1

HCID 697599182-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2.5 g of 2-benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine, 2.3 g of dl-10-camphorsulfonic acid, 20 ml of 2,2-dimethoxypropane and 5.0 ml of N,N-dimethylformamide was stirred at room temperature overnight. Aqueous saturated sodium bicarbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to filtration through silica gel and eluted with ethyl acetate, to give 2.87 g of the target compound.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. customthe solvent was removed
  4. filtrationThen, the residue was subjected to filtration through silica gel
  5. washeluted with ethyl acetate

出典と根拠

ORDレコード
ord-141347c0d4224e4d8930515a0805b62e
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

反応ノート

読み込み中…