Sodium hydride → (S)-1-Benzyl-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidine

HRID 1774747ノート

反応式

HRID 1774747 の反応式
[H-].[Na+].[CH2:3]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][OH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O>C1COCC1>[CH2:3]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][O:16][CH2:22][C:23]([F:26])([F:25])[F:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 719760[(2S)-1-benzylpyrrolidin-2-yl]methanol

生成物 1

HCID 86679127(S)-1-Benzyl-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidine収率 49.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (60% in mineral oil, 0.314 g, 7.84 mmol) in THF (20 mL) was added (S)-(1-benzyl-pyrrolidin-2-yl)-methanol (1.0 g, 5.23 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, 2,2,2-trifluoroethyl methanesulfonate (1.4 g, 7.84 mmol) was added and stirring was continued at room temperature over night. The reaction mixture was quenched with H2O (10 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH(1% NH4OH)-DCM gradient to give the title compound (0.706 g, 37%) as a light yellow liquid. MS: 274.3 (M+H+).

後処理

  1. stirringstirring
  2. waitwas continued at room temperature over night
  3. customThe reaction mixture was quenched with H2O (10 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialCombined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography
  9. washeluting with a 0 to 5% MeOH(1% NH4OH)-DCM gradient

出典と根拠

ORDレコード
ord-1045b6b2241b49d197d088c8ceac86f1
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

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