Reaction #1058309

Reaction equation

Na2CO3

BH3-THF

Boc-MeAla-OH

water

→

product

Yield 98.0%

((S)-2-Hydroxy-1-methyl-ethyl)-methyl-carbamic acid tert-butyl ester

Yield 98.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONwere added carefully at 0-5° C
2. 2
   workup.ADDITIONwere added
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for 1 h
5. 5
   ExtractionThe reaction mixture was extracted with 500 ml and 400 ml ethyl acetate
6. 6
   Washthe organic layers were washed with brine
7. 7
   Dryingdried (Na2SO4)
8. 8
   OtherRemoval of the solvent
9. 9
   Otherby rotary evaporation

Procedure

20.3 g Boc-MeAla-OH (100 mmol; Fluka) were dissolved in 80 ml THF and cooled to 0° C. 150 ml 1M BH3-THF (150 mmol; Fluka) were added at 0° C. over 1 h and after additional stirring at 0° C. for 1 h, 65 ml deionized water were added carefully at 0-5° C. After warming up to RT 160 ml 10% Na2CO3 were added and stirring continued for 1 h. The reaction mixture was extracted with 500 ml and 400 ml ethyl acetate and the organic layers were washed with brine and dried (Na2SO4). Removal of the solvent by rotary evaporation gave 18.5 g (98%) product as a colorless oil, [α]D=−6.1 (CHCl3; c=1). 1H-NMR:

Source