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

HRID 1911521ノート

反応式

HRID 1911521 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 68714982HCID 68714982、化合物収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b63b63a03c6247b786ea3d647a2914ca
出典データセット
uspto-grants-2013_12
特許番号
US08604061B2

反応ノート

読み込み中…