Diisopropylamine → HCID 57279799, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of lithium diisopropylamide was prepared from 1.96 mL (1.42 g) of diisopropylamine and 7.6 mL of n-butyllithium (1.75M in hexane) in 14 mL of THF. The solution was cooled to -78° C. with stirring, combined with a solution of (4S, 5R)-3-(1-oxo-4-methylpentyl)-4-methyl-5-phenyl-2-oxazolidinone (3.50 g) in THF (14 mL) and stirred for 30 min at -78° C. To this mixture was added 2.1 mL (3.1 g) of benzyl bromomethyl sulfide. The reaction mixture was stirred for 2 h at -25° C. and for 2 h at 0° C. Aqueous NH4Cl solution was added to the mixture. The organic solvents were removed in vacuo and the residue was extracted twice with CH2Cl2. The combined organic extract was washed twice with 1M aqueous NaHSO4, then with saturated NaHCO3, brine, dried over Na2SO4 and evaporated. The residue was subjected to flash chromatography on silica gel (hexane-EtOAc) to give 5.0 g (96% yield) of (4S, 5R)-3-[(2S)-1-oxo-2-((benzylthio)methyl)-4-methylpentyl]-4-methyl-5-phenyl-2-oxazolidinone as a clear oil. Characteristic analytical data are as follows: 1H NMR (300 MHz, CDCl3) δ7.24-7.47 (m, 10H), 5.66 (d, J=7 Hz, 1H), 4.81 (p, J= 7 Hz, 1H), 4.31-4.36 (m, 1H), 3.80 (AB q, J=13 Hz, 2H), 2.72 (dd, J=9, 14 Hz, 1H), 2.52 (dd, J=5, 14 Hz, 1H), 1.35-1.71 (m, 3H), 0.89-0.95 (m, 9H); [α]25D -91° (c=2.60, CH2Cl2)

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