Réaction #171114

Équation de réaction

(S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide

HCl

→

title compound

Rendement 106.1%

(S)-4-amino-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium chloride hydrochloride

Rendement 106.1%

Solvants

dioxane

dioxane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred vigorously for another 1 h
2. 2
   LavageThe remaining yellow slurry was rinsed with Et2O
3. 3
   workup.STIRRINGstirred
4. 4
   AutreThe solids were dried under high vacuum

Mode opératoire

To a solution of (S)-4-(tert-butoxycarbonylamino)-5-methoxy-N,N,N-trimethyl-5-oxopentan-1-aminium iodide (20.5 mmol, 1.0 eq) in anhyd dioxane (10 mL), was added HCl (51 mL, 205 mmol, 10 eq, 4M in dioxane). The orange slurry was stirred at room temperature for 1 h, the solids were broken up, then stirred vigorously for another 1 h. The suspension was allowed to settle before cannulating off the dioxane layer. The remaining yellow slurry was rinsed with Et2O, stirred and cannulated out the ether layer (4×). The solids were dried under high vacuum to give the title compound (5.68 g) as a light yellow powder. 1H NMR (400 MHz, DMSO) δ 8.75 (s, 3H), 4.03-3.93 (m, 1H), 3.68 (s, 3H), 3.30-3.20 (m, 2H), 2.98 (s, 9H), 1.89-1.69 (m, 4H); MS (EI) m/z 189 (M+).

Source