Réaction #674318

Équation de réaction

sodium hydride

DMF

alcohol

(R)—N-Boc-2-hydroxypiperidine

DMF

iodomethane

→

(R)—N-Boc-2-methoxymethylpiperidine

Rendement 85.0%

Conditions de réaction

Traitement

1. 1
   Températurewas cooled with ice
2. 2
   workup.ADDITIONwas added
3. 3
   AutreThe mixture was quenched with saturated NH4Cl-solution
4. 4
   Extractionextracted with EtOAc
5. 5
   LavageThe combined organic extracts were washed with brine
6. 6
   Séchagedried over MgSO4
7. 7
   Concentrationconcentrated under reduced pressure

Mode opératoire

A suspension of sodium hydride (0.13 g, 5.4 mmol) in DMF (4 mL) was cooled with ice and a solution of the intermediate alcohol of Step 2 (0.97 g, 4.5 mmol) in DMF (1 mL) was added dropwise. After stirring for 30 min at room temperature iodomethane (0.96 g, 6.8 mmol) was added and the mixture was stirred over night. The mixture was quenched with saturated NH4Cl-solution and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure to leave the crude (R)—N-Boc-2-methoxymethylpiperidine (0.88 g, 85%).

Source