Diisopropylamine → Tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate

HRID 1062821ノート

反応式

HRID 1062821 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].C([O:23][C:24](=O)[CH2:25][CH:26]([OH:30])[CH2:27][C:28]#[N:29])C>O1CCCC1>[C:28]([CH2:27][CH:26]([OH:30])[CH2:25][C:24](=[O:23])[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:29]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 4184461Ethyl 4-cyano-3-hydroxybutanoateHCID 178418339Butyllithium

生成物 1

HCID 11637184Tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-55 °C

実験手順

To a vessel containing 265 kg of 16.8% n-butyllithium is added a mixture of 80 kg of diisopropylamine in 80 L of tetrahydrofuran maintaining the temperature at less than 20° C. The solution is cooled to −55° C., and 85 kg of tert-butyl acetate is added maintaining the temperature at −50°±5° C. A solution of 25 kg of R 4-cyano-3-hydroxybutanoic acid ethyl ester in 55 L of tetrahydrofuran is then added, and the temperature is allowed to warm to −20° C. for at least 20 minutes. The solution is then quenched by transferring to aqueous hydrochloric acid. The organic layer is separated and the aqueous layer re-extracted with ethyl acetate. The combined organic layers are concentrated by vacuum distillation to afford crude 5R 1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate.

後処理

  1. additionis added
  2. temperaturemaintaining the temperature at −50°±5° C
  3. temperatureto warm to −20° C. for at least 20 minutes
  4. customThe solution is then quenched
  5. customThe organic layer is separated
  6. extractionthe aqueous layer re-extracted with ethyl acetate
  7. concentrationThe combined organic layers are concentrated by vacuum distillation

出典と根拠

ORDレコード
ord-a8a1d4d52eb04b8db02c734d6eafe66a
出典データセット
uspto-grants-2005_11
特許番号
US06962994B2

反応ノート

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