Reaction #674318

Reaction equation

sodium hydride

DMF

alcohol

(R)—N-Boc-2-hydroxypiperidine

DMF

iodomethane

→

(R)—N-Boc-2-methoxymethylpiperidine

Yield 85.0%

Conditions

Workup

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

Procedure

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