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

HRID 1774747노트

반응식

HRID 1774747 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-1045b6b2241b49d197d088c8ceac86f1
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260408B2

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