Trimethyl[(1,2,2-triethoxyethenyl)oxy]silane → HCID 118194606, compound
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- additionBF3OEt2 (7.0 mL, 57.0 mmol) was added to the mixture
- stirringthe mixture was stirred at 0° C. for further three hours
- customThe volume of the mixture was halved by evaporation, water
- additionwas added
- customthe phases were separated
- customRemoval of the solvent in vacuo
Sources & evidence
- ORD record
- ord-5fb92813c98a4799a5d90534f890e30e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346853B2
Reaction notes
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