Trifluoroacetic acid → Ethyl trans-1-benzyl-4-(2,2,2-trifluoroethyl)pyrrolidine-3-carboxylate

HRID 577718ノート

反応式

HRID 577718 の反応式
[F:1][C:2]([F:12])([F:11])[CH2:3]/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(O)(C(F)(F)F)=O.[CH2:20]([N:27]([CH2:33]O)[CH2:28][Si](C)(C)C)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH2:20]([N:27]1[CH2:33][C@@H:4]([CH2:3][C:2]([F:11])([F:12])[F:1])[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 15104041Ethyl 5,5,5-trifluoropent-2-enoate2 回HCID 70869782HCID 70869782、化合物

生成物 1

HCID 57556218Ethyl trans-1-benzyl-4-(2,2,2-trifluoroethyl)pyrrolidine-3-carboxylate収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of ethyl (2E)-5,5,5-trifluoropent-2-enoate (3.0 g, 16.5 mmol) and TFA (0.38 g, 3.3 mmol) in DCM (40 mL) was added dropwise {benzyl[(trimethylsilyl)methyl]amino}methanol (7.8 g, 33 mmol) at 0° C. over a period of 30 min. After the addition, the mixture was refluxed overnight. TLC (petroleum ether:EtOAc 10:1) indicated ethyl (2E)-5,5,5-trifluoropent-2-enoate was consumed. The reaction mixture was washed with sat. NaHCO3 (40 mL), brine (40 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=100:1 to 10:1) to give the title compound (5.1 g, 98% yield) as a yellow oil.

後処理

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed overnight
  3. customwas consumed
  4. washThe reaction mixture was washed with sat. NaHCO3 (40 mL), brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=100:1 to 10:1)

出典と根拠

ORDレコード
ord-32089947bf5240b89045271dcf6c6daf
出典データセット
uspto-grants-2015_05
特許番号
US09040547B2

反応ノート

読み込み中…