Water → HCID 59021637, compound

HRID 971127Notes

Reaction equation

HRID 971127 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11](O)=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1.O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:4]([O:3][C:1](=[O:2])[N:8]([C@@H:9]([CH3:10])[CH2:11][OH:12])[CH3:14])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Product 1

HCID 59021637HCID 59021637, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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:

Workup

  1. additionwere added carefully at 0-5° C
  2. additionwere added
  3. stirringstirring
  4. waitcontinued for 1 h
  5. extractionThe reaction mixture was extracted with 500 ml and 400 ml ethyl acetate
  6. washthe organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent
  9. customby rotary evaporation

Sources & evidence

ORD record
ord-7c2e032ddaa740dda151035d7dfee450
Source dataset
uspto-grants-2007_12
Patent number
US07312343B2

Reaction notes

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