Potassium Bromide → tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-Boc-3-pyrrolidinemethanol (5.0 g, 24.8 mmol) in DCM was added TEMPO (80 mg, 0.5 mmol) and potassium bromide (150 mg, 1.3 mmol). This mixture was cooled to 5° C. and vigorously stirred as a pre-chilled (at 0° C.) 1:1 mixture of NaOCl in water (53 mL) and a saturated, aqueous NaHCO3 solution (53 mL) was added dropwise. The resultant mixture was extracted with DCM (3×50 mL). The combined organic layers were washed with water (50 mL) and saturated aqueous NaCl (50 mL). The organic layer was dried over anhydrous Na2SO4 to yield 4.3 g of the title compound, which was used without further purification.

Provenance & Evidence