tert-Butyl bromoacetate → HCID 58280086、化合物

HRID 2189034ノート

反応式

HRID 2189034 の反応式
[C@H:1]1([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]([OH:7])[CH2:2]1.[C:9]([O:13][C:14](=[O:17])[CH2:15]Br)([CH3:12])([CH3:11])[CH3:10]>C1COCC1.ClCCl>[C:9]([O:13][C:14](=[O:17])[CH2:15][O:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:1]([OH:8])[CH2:2]1)([CH3:12])([CH3:11])[CH3:10]

参加物

5

反応物 2

HCID 79177tert-Butyl bromoacetateHCID 6432541HCID 6432541、化合物

生成物 1

HCID 58280086HCID 58280086、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Dissolve 5.0 g (43 mmol) of cis/trans-1,3-cyclohexanediol (approx. 1.2:1 cis/trans mixture) in 20 ml of absolute THF and, at RT, add 24.8 ml (approx. 49.5 mmol) of phosphazene base P2-t-Bu in THF (approx. 2 M solution) dropwise. Stir the solution at RT for a further 30 min and then add dropwise to a mixture of 9.5 ml (64.6 mmol) of bromoacetic acid tert-butyl ester and add 10 ml of THF dropwise. Stir the mixture at RT overnight, then dilute with dichloromethane, and wash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. Separate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1). 2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction.

後処理

  1. stirringStir the mixture at RT overnight
  2. washwash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution
  3. dry with materialdry over sodium sulphate
  4. concentrationconcentrate under reduced pressure
  5. customSeparate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1)
  6. custom2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction

出典と根拠

ORDレコード
ord-97a70ecfc51842bf89cc098d85df5eff
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

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