Water → HCID 53856743, compound
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7](OC)[N:6]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:4].[CH2:23]([Si](C)(C)C)[CH:24]=[CH2:25].O>C(Cl)Cl.[Cl-].[Na+].O.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:25][CH:24]=[CH2:23])[N:6]1[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])=[O:4]Participants
Conditions
- Temperature
- -78 °C
Procedure
6-Methoxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (Compound 233, 1.04 g, 3.39 mmol) was dissolved in CH2Cl2 (10 mL), and the solution was cooled to −78° C. using dry ice-acetone bath. 1M TiCl4 solution in CH2Cl2 (3.7 mL) was added dropwise over a 1-minute period, followed by allyltrimethylsilane (1.61 mL, 10.14 mmol). The bath was changed to water, and the reaction mixture was stirred for 2 hours. The reaction mixture was poured into brine (50 ml) and extracted with CHCl3 (2×50 mL). The combined organic layers were washed with saturated NaHCO3 solution (50 mL) and finally dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography (1:5 EtOAc/hexanes) to give Compound 234 (0.91 g, 84%). Rf=0.78 (1:2 EtOAc/hexanes).
Workup
- extractionextracted with CHCl3 (2×50 mL)
- washThe combined organic layers were washed with saturated NaHCO3 solution (50 mL)
- dry with materialfinally dried over Na2SO4
- customThe solvent was evaporated
- customthe residue was purified by flash chromatography (1:5 EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-667ac87cbfa44ce4a9fd2f332101f691
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06630472B1
Reaction notes
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