Sodium Chloride → HCID 59271881, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methylamine hydrochloride (0.83 kg, 12.34 mol) in water (14.66 L) was added dioxane (24.43 L) and 5-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxy-4-methylpentanal (crude, 2.9 kg, 11.22 mol) and NaCN (0.605 kg, 12.34 mol) over 10 minutes while maintaining the reaction temperature at 15° C. The reaction mixture was stirred overnight, then NaCl (1.7 kg) was added and the layers separated. The aqueous layer was extracted with EtOAc (2×4 L). The combined organic layers were dried over Na2SO4, filtered and concentrated to provide 5.63 kg (>100%) of crude material. To a solution of the crude residue in EtOAc (20 L) at 6° C. was added di-tert-butyldicarbonate (2.57 kg, 11.78 mol) in 1.5 L of EtOAc via additional funnel over 5 minutes. The reaction mixture was stirred at 15° C. overnight and concentrated in vacuo. Flash column chromatography eluted with 0 to 30% EtOAc in heptane provided the desired product.

Provenance & Evidence