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Synthesis of furfurylamine

May 18，2023

Furfurylamine (FLA) is a key furan-based compound for the production of food additives, fuel additives, polymers, fibers, perfumes, and pharmaceuticals. It can be obtained by amination of furfural by ω-transaminase (AtAT) from Aspergillus terreus.

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Furfurylamines have many applications as monomers in biopolymer synthesis and for the preparation of pharmacologically active compounds, although preparation via traditional synthetic routes is not straightforward due to by-product formation and sensitivity of the furan ring to reductive conditions.

Synthesis of furfurylamine

4-Methylbenzaldehyde (24 mg, 0.2 mmol), methyl carbamate (30 mg, 0.4 mmol), TFA (91 mg, 0.8 mmol) and TBDMSH (114 mg, 0.8 mmol) were dissolved in MeCN (4.0 mL) and heated to 150 °C for 15 min in a Smith SynthesizerTM microwave apparatus. The mixture was concentrated in vacuo and the residue was dissolved in a mixture of THF, MeOH and 2M LiOH (1:1:1, 4 mL) and heated at 120 °C for 10 min in a Smith SynthesizerTM. EtOAc (4 mL) and 1M NaOH (4 mL) were added and the phases were separated. The organic phase was extracted with 1M HCl (2 × 4 mL) and the aqueous extract was evaporated to afford 4-methylbenzylamine as its hydrochloride salt. The purity of this material was at least 99% as determined by LC-MS. 2-Furfurylmethylamine, yield 77%. 1H NMR (400 MHz, CD3OD): δ = 4.19 (s, 2 H), 6.48 (d, J= 7.5 Hz, 1 H), 6.58-6.61 (m, 1 H), 7.62 (d, J= 6.8 Hz, 1 H). MS (ES+): m/z= 98 [M + H]+.

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