Chloroform → 5-Chloro-6-hydroxymethyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Participants

Reaction Steps

The product of step c) (185 mg, 0.74 mmol) was dissolved in CHCl3 (2.7 ml) and a solution of SO2Cl2 (59.5 μl, 0.74 mmol) in CHCl3 (1 ml) was added dropwise over 10 minutes and the contents were stirred for 1 hour. Next, the mixture was diluted with CH2Cl2 (10 ml), washed with H2O (2×25 ml), sat. NaHCO3 (25 ml) and dried (MgSO4). The crude residue was purified by preparative TLC (hexanes/EtOAc-1:3) to give the subtitle compound (99.7 mg, 45%). 1H NMR (300 MHz, CDCl3, ppm) 1.20 (t, J=7 Hz, 3H); 2.37 (br s, 1H); 2.65-2.71 (m, 1H); 2.90-3.05 (m, 1H); 3.08-3.18 (br m, 1H); 3.28-3.42 (br m, 1H); 3.52-3.72 (br m, 2H); 3.75-3.88 (m, 2H); 4.09 (q, J=7 Hz, 2H); 4.54 (s, 2H).

Provenance & Evidence