Methanol → Methyl-5-methoxy-3-aminovalerate

Methyl-5-methoxy-3-oxovalerate (10 g, 62.5 mmol) was added to methanol (200 ml) followed by ammonium formate (39.4 g, 620 mmol) and NaBH3CN (3.9 g, 46 mmol) at 25° C. After 24 h the methanol was removed in vacuo to leave a white mass. Methylene chloride was added and the mixture filtered. The methylene chloride was evaporated resulting in an oil which was dissolved in 1N HCl (200 ml) and extracted with ether (100 ml). The ether layer was discarded and the aqueous layer was made basic using solid K2CO3. The product was extracted into methylene chloride dried over Na2SO4 and evaporated to give methyl-5-methoxy-3-aminovalerate (7.5 g). 1H NMR (d6-DMSO) δ 1.25 (m, 3H) 1.66 (m, 2H), 1.86 (bs, 2H), 2.9 (M, 2H), 3.33 (s, 3H), 3.49 (M, 2H), 3.7 (s, 3H); MS (FAB) m/z 161.2 (MH+).

1. customAfter 24 h the methanol was removed in vacuo
2. customto leave a white mass
3. filtrationthe mixture filtered
4. customThe methylene chloride was evaporated
5. customresulting in an oil which
6. extractionextracted with ether (100 ml)
7. extractionThe product was extracted into methylene chloride
8. dry with materialdried over Na2SO4
9. customevaporated

ORD record

ord-fc4a5955794646d68a4c24dff9d68ac1

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05344957