tert-Butanol → HCID 22335628, compound

Participants

Reaction Steps

7-(4-Chlorophenyl)-6-phenyl-2,3-dihydro-1H-pyrrolizine (Example 21 b, 0.75 g, 2.5 mmol), dissolved in THF (10 ml), is treated with triethylamine (0.3 ml, 0.25 g, 2.5 mmol). A solution of diphosgene (0.25 g, 1.25 mmol), dissolved in THF (5 ml), is added dropwise to this solution at RT, and it is stirred for 18 h. tert-Butyl alcohol (abs., 1.0 ml, 0.786 g, 10 mmol) and triethylamine (0.7 ml, 0.51 g, 5 mmol) are then added, and the mixture is stirred at RT for a further 48 h. The reaction mixture is partitioned between water (30 ml) and CHCl3 (60 ml), and the ether phase is washed with Na2CO3 solution (5%, 20 ml). After removal of the solvent in vacuo, an oily residue (0.7 g), which by TLC (SiO2, hexane/CH2Cl2 1:1) still contains starting material (Rf 0.75) in addition to product (Rf 0.3), is obtained from the THF/CHCl3 phase dried using Na2SO4 sicc. The residue is purified by CC (SiO2, hexane/CH2Cl2 1:1); 190 mg of the pure ester are obtained.

Provenance & Evidence