Methyl chloroformate → HCID 86702798, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1R,4S)-7-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid (L) (2.33 g, 7.30 mmol) in THF (50 mL) was added N-methylmorpholine (2.00 mL, 18.25 mmol). The mixture was cooled to −25° C. before adding methyl chloroformate (1.41 mL, 18.25 mmol) dropwise. The mixture was stirred at −25° C. for 20 minutes and the solid was removed by filtration. The solution was carefully added to a solution of NaBH4 (1.65 g, 43.80 mmol) in water (100 mL) at 0° C. The mixture was stirred for 1 hour at room temperature. The acetone was removed under vacuum and the aqueous phase was extracted with EtOAc (×3). The combined organic phases were washed with 1 M NaOH, dried over MgSO4 and concentrated under vacuum to give (1R,4S)-benzyl 2,3-bis(hydroxymethyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (LI) as a colorless oil (1.85 g, 6.35 mmol, 87% yield). 1H NMR (CDCl3) δ ppm 1.40 (brs, 1H), 1.54 (brs, 1H), 1.63 (brs, 2H), 1.81 (brs, 1H), 1.98 (brs, 1H), 3.50-3.56 (m, 1H), 3.58-3.67 (m, 2H), 3.69-3.78 (m, 1H), 4.10 (brs, 2H), 5.09 (brs, 2H), 7.34 (brs, 5H); ESIMS found for C16H21NO4 m/z 292 (M+H).

Provenance & Evidence