Reaction #48673

Reaction equation

[(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

sodium hydride

→

desired compound

(S)-5-benzyloxymethyl-2,2-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Solvents

ethyl acetate

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureHeat
2. 2
   Otherreaction mixture to 60° C. for 4 hours
3. 3
   WashWash with water and saturated aqueous sodium chloride
4. 4
   Dryingdry (magnesium sulfate)
5. 5
   Filtrationfilter
6. 6
   Concentrationconcentrate
7. 7
   OtherPurify on silica gel eluting with 0:100 to 20:80 ethyl acetate

Procedure

To [(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester (4.74 g, 8.07 mmol) in N,N-dimethylformamide (70 mL) at room temperature add sodium hydride (0.452 g, 11.3 mmol, 60% dispersion in mineral oil). Heat reaction mixture to 60° C. for 4 hours, cool to room temperature and dilute with ethyl acetate (˜400 mL). Wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify on silica gel eluting with 0:100 to 20:80 ethyl acetate:hexanes to give the desired compound as an oil.

Source