Reaction #74437

Reaction equation

5-isopropyl-5-methyl-2-((1R,2S,4R)-5-oxobicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one

L-Selectride

→

title compound

2-((1R,2S,4R,5R)-5-Hydroxybicyclo[2.2.1]heptan -2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one

Solvents

THF

THF

Conditions

Workup

1. 1
   Otherthe reaction was quenched with hydrogen peroxide (35 wt % solution in water, 4 mL) and NaOH (10% aqueous, 7 mL)
2. 2
   TemperatureThe mixture was warmed to ambient temp.
3. 3
   Otherin a 65° C.
4. 4
   Otherovernight
5. 5
   OtherThe volatiles were removed in vacuo
6. 6
   OtherThe residue was partitioned between CHCl3/i-PrOH (v/v=3/1) and brine
7. 7
   OtherThe organic portion was separated
8. 8
   Dryingdried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    OtherThe residue was purified by flash column chromatography (0 to 5% of MeOH in EtOAc)

Procedure

To a solution of 5-isopropyl-5-methyl-2-((1R,2S,4R)-5-oxobicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (0.380 g, 1.36 mmol) in anhydrous THF (20 mL) was added L-Selectride (1.0 M solution in THF, 4.07 mL, 4.07 mmol) in anhydrous THF at −78° C. under nitrogen. After stirring at −78° C. for 3 h., the reaction was quenched with hydrogen peroxide (35 wt % solution in water, 4 mL) and NaOH (10% aqueous, 7 mL). The mixture was warmed to ambient temp. and then in a 65° C. bath overnight. The volatiles were removed in vacuo. The residue was partitioned between CHCl3/i-PrOH (v/v=3/1) and brine. The organic portion was separated, dried over MgSO4, filtered, and conc. in vacuo. The residue was purified by flash column chromatography (0 to 5% of MeOH in EtOAc) to give the title compound as a white solid.

Source