Tetrahydrofuran → Benzyl 4-(3,3,3-trifluoro-2-hydroxypropoxy)piperidine-1-carboxylate

HRID 2368102ノート

反応式

HRID 2368102 の反応式
[O:1]=[CH:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.C[Si](C)(C)[C:23]([F:26])([F:25])[F:24].C1COCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:24][C:23]([F:26])([F:25])[CH:2]([OH:1])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

生成物 1

HCID 67447074Benzyl 4-(3,3,3-trifluoro-2-hydroxypropoxy)piperidine-1-carboxylate収率 63.9%

試薬・触媒・溶媒 2

HCID 2724141Tetrabutylammonium Fluoride触媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate (2.00 g), trimethyl(trifluoromethyl)silane (1.23 g), tetrabutylammonium fluoride (1 M THF solution, 1 drop) and THF (20 mL) was stirred at 0° C. for 1 hr, and then at room temperature for 3 days. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in THF (20 mL). Tetrabutylammonium fluoride (1 M THF solution, 8.65 mL) was added thereto at 0° C., and the obtained mixture was stirred at 0° C. for 2 hr. 1M Hydrochloric acid was added, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.60 g).

後処理

  1. waitat room temperature for 3 days
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in THF (20 mL)
  7. additionTetrabutylammonium fluoride (1 M THF solution, 8.65 mL) was added
  8. stirringat 0° C., and the obtained mixture was stirred at 0° C. for 2 hr
  9. addition1M Hydrochloric acid was added
  10. extractionthe obtained mixture was extracted with ethyl acetate
  11. washThe extract was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-566cee4141ea4dc2b2c6008a677c7344
出典データセット
uspto-grants-2014_04
特許番号
US08703758B2

反応ノート

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