in ethanol T=20°C; 0.166667 h;

1: (3R,7aS)-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2 h; 2: methyl iodide in tetrahydrofuran T=-78 - 20°C; 4 h;

1: 60 percent / ethanol / 0.17 h / 20 °C 2: 70 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

in ethanol T=20°C; 0.166667 h;

1: 69 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 to -30 deg C, 2 h 2: 90 percent / HCl, H2O / 1 h / Heating View Scheme

1: 72 percent / acetonitrile / 1 h / 20 °C 2: 77 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.83 h / -78 °C 1.2: 63 percent / tetrahydrofuran / 2 h / -78 - -50 °C 2.1: 100 percent / thionyl chloride / 3 h / Heating 3.1: 92 percent / triethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH2Cl2 / 20.5 h / 20 °C 4.1: 90 percent / aqueous sodium hydroxide / dioxane / 19 h / 20 °C View Scheme

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 °C / Inert atmosphere 2.1: acetyl chloride / 20 h / Reflux; Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: water; sodium hydroxide / methanol / 3 h / 50 °C / Inert atmosphere View Scheme

1: LDA / tetrahydrofuran / -78 °C 2: HCl; NaHCO3 View Scheme