Water → (2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol

HRID 57362Notes

Reaction equation

HRID 57362 reaction equation
C(OC(=O)[NH:10][C@@H:11]([C@@H:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:15])[CH2:12][OH:13])C1C=CC=CC=1.[H][H].O>[Pd].CO>[NH2:10][C@@H:11]([C@@H:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH3:15])[CH2:12][OH:13]

Participants

6

Reactant 3

HCID 962WaterHCID 131736954HCID 131736954, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 90414285(2R,3S)-2-amino-3-(tert-butoxy)butan-1-olYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a round bottom flask containing benzyl((2R,3S)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate (5.27 g, 17.8 mmol) was added MeOH (100 mL). Solution was degassed with nitrogen for 15 min at which time palladium on carbon (0.95 g, 0.89 mmol) in MeOH (5 mL) was added. A hydrogen atmosphere was then inserted. Resulting reaction mixture allowed to stir 40 min at room temperature at atmospheric pressure when water (2 mL) was added and once again a hydrogen atmosphere was inserted at atmospheric pressure and the subsequent reaction mixture allowed to stir 18 hr at room temperature. The reaction mixture was filtered through a pad of celite and concentrated to a brown oil. Oil redissolved in toluene and concentrated to afford (2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol (2.5 g, 15.5 mmol, 87% yield) as a brown oil. LCMS m/z 162.1 (M+H)+, Rt 0.41 min (Mass ion only, no UV peak).

Workup

  1. additionwas added
  2. customResulting
  3. customreaction mixture
  4. additionwas added
  5. filtrationThe reaction mixture was filtered through a pad of celite
  6. concentrationconcentrated to a brown oil
  7. dissolutionOil redissolved in toluene
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-245254501b2648ca98bbfdc18852d536
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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