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

HRID 1180115

반응식

HRID 1180115 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-20047f658506466f89d50a259df1cdfb
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279584B2

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