Reaction #50044

Reaction equation

compound

N-Cbz-L-proline

dimethyl sulfide

→

title product

Yield 98.0%

N-Cbz-L-prolinol

Yield 98.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturecooled to 0° C.
2. 2
   Otherquenched by careful addition of 10% acetic acid in methanol
3. 3
   OtherThe mixture was reduced in volume on a rotary evaporator
4. 4
   workup.DISSOLUTIONthe concentrate was dissolved in ethyl acetate
5. 5
   Washwhich was washed successively with 1N HCl, water and sodium bicarbonate solution
6. 6
   ExtractionThe organic extract
7. 7
   Dryingwas dried over Na2SO4
8. 8
   Concentrationconcentrated

Procedure

A 21.56 g (86.55 mmol) sample of the compound from step 24a above was dissolved in 200 mL of THF, and the solution was cooled to 0° C. BH3 -dimethyl sulfide (86.5 mL, 2N) was added dropwise under a nitrogen atmosphere. The reaction was stirred at room temperature for 16 hr, then cooled to 0° C. and quenched by careful addition of 10% acetic acid in methanol. The mixture was reduced in volume on a rotary evaporator, and the concentrate was dissolved in ethyl acetate, which was washed successively with 1N HCl, water and sodium bicarbonate solution. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 19.94 g (98% yield).

Source