Reaction #2275689

Reaction equation

Triethylamine

Tris hydrochloride

2,2-dimethoxypropane

para-toluenesulfonic acid

→

product

Yield 85.0%

(5-Amino-2,2-dimethyl-[1,3]dioxan-5-yl)-methanol

Yield 85.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otherresulted
2. 2
   Othersolvent evaporated
3. 3
   workup.DISSOLUTIONThe viscous crude was dissolved in triethylamine (40 ml)
4. 4
   workup.ADDITIONethyl acetate (750 ml) added
5. 5
   Filtrationthe white precipitate of ammonium salts was filtered off
6. 6
   workup.STIRRINGafter stirring for 30 mins
7. 7
   OtherThe filtrate was evaporated

Procedure

Tris hydrochloride (51 g, 324 mmol) was suspended in dry DMF (100 ml) and 2,2-dimethoxypropane (39 g, 374 mmol) was added followed by para-toluenesulfonic acid (2.6 g, 13.5 mmol). The mixture was stirred in a sealed flask for 18 h at ambient temperature when a clear solution resulted. Triethylamine (2.5 ml) was added and solvent evaporated. The viscous crude was dissolved in triethylamine (40 ml) and ethyl acetate (750 ml) added and the white precipitate of ammonium salts was filtered off after stirring for 30 mins. The filtrate was evaporated to give the product as a colourless liquid in approx. 85% yield.

Source