Reaction #1857562

Reaction equation

tert-butyl ((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)carbamate

HCl

dioxane

→

(3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-aminium chloride

Solvents

DCM

Conditions

Workup

1. 1
   OtherThe solvent was removed under a stream of N2, which
2. 2
   Otherafforded a white solid
3. 3
   OtherThis solid was triturated with Et2O (3×3 mL)
4. 4
   Otherthe resulting powder was dried under high vacuum for 1 h

Procedure

To a solution of tert-butyl ((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)carbamate (330 mg, 0.826 mmol) in DCM (3 mL) was added a solution of HCl in dioxane (2.07 mL, 8.26 mmol, 4M) under N2 and the resulting solution was stirred at room temperature for 2 h. The solvent was removed under a stream of N2, which afforded a white solid. This solid was triturated with Et2O (3×3 mL) and the resulting powder was dried under high vacuum for 1 h to give (3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-aminium chloride (59): ESIMS m/z 300 ([M+H]+).

Source