Sodium Fluoride → (2S,4S)-1-Benzyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

HRID 1180115

反応式

HRID 1180115 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14](O)[CH2:13][C@H:12]1[C:17]([O:19][CH3:20])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Na+].C(N(/C(/F)=C(\F)/C(F)(F)[F:31])CC)C.C(N(C(F)(F)C(F)C(F)(F)F)CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([F:31])[CH2:13][C@H:12]1[C:17]([O:19][CH3:20])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 5235Sodium FluorideHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 131726637HCID 131726637、化合物

生成物 1

HCID 11637722(2S,4S)-1-Benzyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate収率 74.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl(2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (306 mg, 0.00108 mol) and sodium fluoride (55 mg, 0.00131 mol) were suspended in dichloromethane (1.8 mL), followed by addition of Ishikawa reagent (293 mg, 0.00131 mol) under ice cooling. The reaction mixture was slowly warmed to room temperature and then stirred for 20 hours. After the reaction, the reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate (5 mL) and then separated into organic and aqueous layers. The aqueous layer was extracted with ethyl acetate. This extracted solution was combined with the organic layer obtained above, washed sequentially with 10% aqueous potassium bisulfate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. After drying, the solvent and the decomposition product of Ishikawa reagent (N,N-diethyl-2,3,3,3-tetrafluoropropionamide) were distilled off under reduced pressure, and the residue was applied to silica gel column chromatography (developing solvent; hexane:ethyl acetate=5:1 to 0:1) to give the titled compound (227 mg, colorless oil).

後処理

  1. customAfter the reaction
  2. customseparated into organic and aqueous layers
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customobtained above,
  5. washwashed sequentially with 10% aqueous potassium bisulfate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter drying
  8. distillationthe solvent and the decomposition product of Ishikawa reagent (N,N-diethyl-2,3,3,3-tetrafluoropropionamide) were distilled off under reduced pressure

出典と根拠

ORDレコード
ord-20047f658506466f89d50a259df1cdfb
出典データセット
uspto-grants-2007_10
特許番号
US07279584B2

関連ノート

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