Ninhydrin → Methyl (R)-2-Amino-3-(trimethylsilyl)propanoate

Participants

Reaction Conditions

Reaction Steps

3-Trimethylsilyl alanine (J. Organomet. Chem., 628, (2001), 183–194; 19 mg, 0.118 mmol) was mixed with 3 ml BF3-MeOH (14%, 3.7 mmol) in a sealed tube and heated to 70° C. Analysis was performed using TLC (MeOH:DCM 1:9, stained w. ninhydrine in ethanol). The mixture was heated for 3 h and was then cooled to ambient temperature. The mixture was poured into a mixture of 3 ml EtOAc and 2 ml water containing Na2CO3. More Na2CO3 (5%-aq) was added until pH ca 7. The aqueous phase was washed with EtOAc (2×3 ml). The combined organic layers were washed with brine (1 ml), dried with Na2SO4 and evaporated. The product was obtained as a white film. Mass: 19 mg (92% yield). NMR (CDCl3): 0.1 (s, 9H), 1.2–1.4 (m, 2H), 3.8 (s, 3H), 4.2 (brs, 1H).

Provenance & Evidence