Trimethyl[(1,2,2-triethoxyethenyl)oxy]silane → HCID 118194606、化合物

HRID 529281ノート

反応式

HRID 529281 の反応式
[CH:1](=[N:5]/[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])\[CH2:2][CH2:3][CH3:4].C[Si](C)(C)[O:16][C:17]([O:25][CH2:26][CH3:27])=[C:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CC1CCCO1>[CH2:23]([O:22][C:18]([O:19][CH2:20][CH3:21])([C@@H:1]([NH:5][C@H:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[CH2:2][CH2:3][CH3:4])[C:17]([O:25][CH2:26][CH3:27])=[O:16])[CH3:24]

参加物

4

反応物 2

HCID 12614350Trimethyl[(1,2,2-triethoxyethenyl)oxy]silaneHCID 178449166HCID 178449166、化合物

生成物 1

HCID 118194606HCID 118194606、化合物収率 119.2%

試薬・触媒・溶媒 1

HCID 73012-Methyltetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

With BF3OEt2: (S,E)-N-butylidene-1-phenylethanamine (Example 1, 10.0 g, 57.0 mmol) was dissolved in 250 mL 2-methyltetrahydrofuran and cooled to 0° C. BF3OEt2 (7.0 mL, 57.0 mmol) was added to the mixture followed by a solution of trimethyl((1,2,2-triethoxyvinyl)oxy)silane (Example 10, 11.34 g, 45.6 mmol) in 80 mL 2-methyltetrahydrofuran, and the mixture was stirred at 0° C. After four hours, further imine (1.8 g, 10.2 mmol) and BF3OEt2 (1.2 mL, 9.7 mmol) were added and the mixture was stirred at 0° C. for further three hours. The volume of the mixture was halved by evaporation, water was added, the mixture was neutralized (pH=7.2) with 2N NaOH, and the phases were separated. Removal of the solvent in vacuo yielded 19.1 g crude (S)-ethyl 2,2-diethoxy-3-(((S)-1-phenylethyl)amino)hexanoate as a 85.15 (syn:anti) diastereomeric mixture.

後処理

  1. additionBF3OEt2 (7.0 mL, 57.0 mmol) was added to the mixture
  2. stirringthe mixture was stirred at 0° C. for further three hours
  3. customThe volume of the mixture was halved by evaporation, water
  4. additionwas added
  5. customthe phases were separated
  6. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-5fb92813c98a4799a5d90534f890e30e
出典データセット
uspto-grants-2016_05
特許番号
US09346853B2

反応ノート

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