Reacción #171114

Ecuación de reacción

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

HCl

→

title compound

Rendimiento 106.1%

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

Rendimiento 106.1%

Disolventes

dioxane

dioxane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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+).

Fuente