Trimethyl[(1,2,2-triethoxyethenyl)oxy]silane → HCID 118194606, 화합물

HRID 529281노트

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HRID 529281 반응식
[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]

참가 물질

4

반응물 2

HCID 12614350Trimethyl[(1,2,2-triethoxyethenyl)oxy]silaneHCID 178449166HCID 178449166, 화합물

생성물 1

HCID 118194606HCID 118194606, 화합물수율 119.2%

시약·촉매·용매 1

HCID 73012-Methyltetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5fb92813c98a4799a5d90534f890e30e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346853B2

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