Dimethylformamide → HCID 67151639、化合物

HRID 1805237

反応式

HRID 1805237 の反応式
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][N:23](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:22]#[N:23])=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67151639HCID 67151639、化合物収率 55%

試薬・触媒・溶媒 1

HCID 11186Zinc cyanide (Zn(CN)2)触媒

実験手順

A stirred solution of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (200 mg, example 1(e)), zinc cyanide (66 mg) and tetrakis(triphenyl-phosphine)palladium (57 mg) in DMF (4 ml) under an argon atmosphere in a sealed tube was heated at 160° C. for 15 minutes under microwave irradiation. The mixture was then poured onto ice-water and the mixture extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-(4-cyano-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (82 mg, 55%) as a colourless viscous oil. MS (ISP): 325.4 ([M+Na]+), 303.4 ([M+H]+), 247.3 ([M+H—C4H8]+).

後処理

  1. additionThe mixture was then poured onto ice-water
  2. extractionthe mixture extracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

出典と根拠

ORDレコード
ord-99793e271f9046a3abb2050b00126617
出典データセット
uspto-grants-2013_01
特許番号
US08354441B2

関連ノート

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