Potassium Carbonate → HCID 19025070, compound

Participants

Reaction Steps

This half-ester R-3k (104 mg; 0.4 mmol) was dissolved in methanol (5 mL) and treated with potassium carbonate (110 mg; 0.8 mmol; 2 equiv.) and stirred overnight to completely consume 3k (tlc analysis). The reaction mixture was diluted with water (25 mL) and ether (25 mL) and the layers were separated. The aqueous layer was extracted with ether (2×15 mL). The combined organic solution was dried (MgSO4) and concentrated to afford 62 mg (94%) of R-1k. All achiral properties of 1k are as reported above. [α]D20 -14.2° (C. 1.01, CH3OH). The absolute configuration of 1k was inferred to be R-(-) by analogy with the absolute configuration results of the enzymatic reaction of 1j. 1H nmr analysis of the MTPA ester using an analogous procedure to that of Dale et al., J. Org. Chem., 1969, 34, 2543, indicated 54% ee for R-1k.

Provenance & Evidence