N,N,N',N'-Tetramethylethylenediamine → 3-Boc-4(S)-Cyclohexylmethyl-2,2-dimethyl-5(R,S)-[2-(4(S,S)-sec.-butyloxazolin-2-yl)ethyl]oxazolidine

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Reaction Steps

3.76 g of 4(S,S)-sec.-butyl-2-methyloxazoline and 4.0 ml of N,N,N',N'-tetramethylethylenediamine are dissolved in 100 ml of THF and, at -78° C., added dropwise to 14.9 ml of a 1.6M solution of n-butyllithium in hexane are added dropwise. The mixture is stirred at this temperature for 30 min and then 1.15 g of 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidine in 10 ml of THF are added dropwise. The reaction solution is stirred at R.T. for 1 h and is poured into 200 ml of saturated aqueous NaHCO3 solution, and the mixture is extracted 3 times with 200 ml of EA. Drying over Na2SO4 and concentration in vacuo is followed by chromatography on silica gel (mobile phase MTB/diisopropyl ether 1:1). The title compound is obtained as a colorless oil.

Provenance & Evidence