Dimethylformamide → 9H-Xanthene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester

HRID 458892

反応式

HRID 458892 の反応式
[CH:1]1[C:14]2[CH:13]([C:15]([OH:17])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:29][N:30]1[CH2:34][CH2:33][C@@H:32](O)[CH2:31]1>C(Cl)(Cl)Cl>[CH3:29][N:30]1[CH2:34][CH2:33][C@@H:32]([O:16][C:15]([CH:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:6][C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:17])[CH2:31]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 65736Xanthene-9-carboxylic acidHCID 69513321-Methyl-3-pyrrolidinol, (-)-

生成物 1

HCID 866022589H-Xanthene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester収率 93%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒3 回

反応条件

温度
0 °C

実験手順

2 g of 9H-Xanthene-9-carboxylic acid (0.0088 mol) were dissolved in 30 ml of CHCl3 (ethanol free). The solution was cooled at 0° C. and 1.08 ml (0.0123 mol) of oxalyl chloride and a drop of DMF was added. The mixture was stirred and allowed to warm to room temperature. After an hour at this temperature the solvents were evaporated and the residue was dissolved in CHCl3 and evaporated again. This procedure was repeated two times. The solid obtained (2.19 g) was dissolved in 20 ml of CHCl3 and added to a solution of 0.975 g (0.0097 mol) of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19) in 15 ml of CHCl3 cooled at 0–5° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The solvent was evaporated and the residue was dissolved in toluene and extracted with HCl 2N. The aqueous layer was basified with K2CO3 and extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to yield 2.53 g (93%) of the title product as an oil.

後処理

  1. temperatureto warm to room temperature
  2. customAfter an hour at this temperature the solvents were evaporated
  3. dissolutionthe residue was dissolved in CHCl3
  4. customevaporated again
  5. customThe solid obtained (2.19 g)
  6. temperaturecooled at 0–5° C
  7. temperatureto warm to room temperature
  8. stirringstirred overnight
  9. customThe solvent was evaporated
  10. dissolutionthe residue was dissolved in toluene
  11. extractionextracted with HCl 2N
  12. extractionextracted with CHCl3
  13. washThe organic layer was washed with brine
  14. dry with materialdried over Na2SO4
  15. customevaporated to dryness

出典と根拠

ORDレコード
ord-2d3ecfc79f2d4888bf50706c464f5c8f
出典データセット
uspto-grants-2007_03
特許番号
US07192978B2

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