Oxalic Acid → HCID 86731689, compound

Participants

Reaction Steps

To a solution of benzyl (2-azido-3,3,3-trifluoropropyl)carbamate (107 g, 371 mmol) in tetrahydrofuran (1000 mL) was added cobalt chloride (17.8 g, 137 mmol) followed by sodium borohydride (1.0 M in water, 1.5 L, 1.5 mol) dropwise over a period of 2 hours. After 2 hours post-addition, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (3×200 mL). The organics were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. To the residue was added oxalic acid (0.37 M solution in ethyl acetate, 1.5 L, 560 mmol). After 16 hours, the reaction mixture was filtered to afford benzyl (2-amino-3,3,3-trifluoropropyl)carbamate oxalic acid salt. The material was used without further purification.

Provenance & Evidence