(R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate → HCID 68714982, 화합물

HRID 1911521노트

반응식

HRID 1911521 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])([CH3:14])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 10977654(R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylateHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 68714982HCID 68714982, 화합물수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (R)-4-acetyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.80 g, CAS 167102-63-8) in THF (40 ml) was cooled under an argon atmosphere to 0° C. and treated dropwise with benzylmagnesium chloride solution (1 M in diethylether, 34.5 ml). The reaction mixture was stirred at r.t. overnight, then quenched with saturated aqueous NH4Cl (50 ml) and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 3:1) to give (R)-4-(1-hydroxy-1-methyl-2-phenyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.45 g, 89%) as off-white waxy solid.

후처리

  1. customquenched with saturated aqueous NH4Cl (50 ml)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 3:1)

출처 및 근거

ORD 기록
ord-b63b63a03c6247b786ea3d647a2914ca
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604061B2

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