Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 16220291, compound

Temperature

-78 °C

A vigorously stirred slurry of ethyl 1,3-dithiolane-2-carboxylate (8, 1.50 mL, 10.5 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.57 g, 26.2 mmol) in THF (21 mL) was treated dropwise with isopropylmagnesium bromide (52.5 mmol, 26.3 mL, 2 M in THF) over 40 min at −78° C. under argon. The reaction mixture was stirred for 1 h at −78° C. under argon. The reaction mixture was quenched with saturated aqueous NH4Cl/H2O (1:1). The aqueous phase was extracted with ether (3×100 mL). The combined organic extract was washed (water, brine), dried (Na2SO4), concentrated and chromatographed [silica, EtOAc/hexanes (2:1)] to afford a yellow oil that solidified upon storage at 1° C. (985 mg, 49%). The characterization values (1H NMR, 13C NMR, ESI-MS) were consistent with those for the title compound prepared via a different synthetic route.43

1. customThe reaction mixture was quenched with saturated aqueous NH4Cl/H2O (1:1)
2. extractionThe aqueous phase was extracted with ether (3×100 mL)
3. extractionThe combined organic extract
4. washwas washed (water, brine)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customchromatographed [silica, EtOAc/hexanes (2:1)]
8. customto afford a yellow oil
9. customthat solidified upon storage at 1° C.

ORD record

ord-5caa268616854f548723996b9ab69993

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365722B2