Reaction equation
[O:1]=[C:2]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3]1.[CH3:18][Si:19]([CH2:22][Mg]Cl)([CH3:21])[CH3:20]>CCOCC>[CH3:18][Si:19]([CH2:22][C:11]1([OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3][C:2]1=[O:1])([CH3:21])[CH3:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (5.02 g, 20.81 mmol) is dissolved in ether (50 mL), and cooled to 0° C. Trimethylsilylmethylmagnesium chloride (42.0 mL of a 1.0M solution in ether, 42.0 mmol) is added dropwise, the reaction is stirred at 0° C. for 20 minutes, and then heated to reflux overnight. The reaction is quenched with saturated ammonium chloride, and extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give separately the two diastereomers of ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate; major isomer, m.p. 129°-130° C.; minor isomer, m.p. 175°-177° C.
Workup
- temperatureheated
- temperatureto reflux overnight
- customThe reaction is quenched with saturated ammonium chloride
- extractionextracted several times with ethyl acetate
- dry with materialThe combined organic layers are dried (Na2SO4)
- customthe solvent is evaporated
- customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-d4fb9e46ad954be7a349fa818cd8a137
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05244889
Linked notes
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