Pyridine → 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester

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Reaction Steps

Chromium (vi) oxide (800 mg, 8.0 mmol) was added to pyridine (1.6 mL) in CH2Cl2 (10 mL) and the resulting solution was stirred for 15 min at room temperature. A solution of tert.butyl-3-hydroxy-1-pyrrolidinecarboxylate (374.5 mg, 2.0 mmol) in CH2Cl2 (5 mL) was added, immediately followed by acetic anhydride and the reaction mixture kept at room temperature for 15 min. After addition of ethyl acetate, decanted and filtered through a short column of silica gel. The filtrate was concentrated to give the subtitled product (193 mg) and was used directly in the next step.

Provenance & Evidence