Tetrabutylammonium Fluoride → HCID 59614360, 화합물

HRID 409471노트

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HRID 409471 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([O:15][Si](C(C)(C)C)(C)C)[C@@H:9]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([OH:15])[C@@H:9]1[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 59614342HCID 59614342, 화합물

생성물 1

HCID 59614360HCID 59614360, 화합물수율 100.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (2S,3S,5R)-2-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.243 mmol; 102 mg) in THF is added 1.0 M THF solution (0.36 mL) of tetra-n-butylammonium fluoride under nitrogen at room temperature. After 3 hours, The reaction mixture is quenched with saturated aqueous ammonium chloride solution, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (74.4 mg, 99%); ESI-MS m/z: 250 [M+−tBu+2], Retention time 2.34 min (condition A).

후처리

  1. customThe reaction mixture is quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

출처 및 근거

ORD 기록
ord-c363b3fc180f41ceabbb3bd75639f8f2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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