Ceric ammonium nitrate → HCID 57979784, compound

HRID 1868023Notes

Reaction equation

HRID 1868023 reaction equation
O=[CH:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[NH2:13][CH2:14][C@H:15]([OH:17])[CH3:16].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CO.[Pd]>[OH:17][C@H:15]([CH3:16])[CH2:14][NH:13][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 439938(2R)-1-aminopropan-2-olHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 57979784HCID 57979784, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-tert-butyl 1-oxopropan-2-ylcarbamate (Boc-L-Alaninal) (3.0 g, 17.32 mmol) and (R)-1-aminopropan-2-ol (1.95 g, 25.98 mmol) in anhydrous methanol (120 mL) was hydrogenated at 1 atmosphere overnight using palladium, 10% wt. on activated carbon (900 mg) as catalyst. Reaction was complete as determined by TLC using CAN spray to visualize. The reaction mixture was then filtered through a celite bed. After solvent evaporation crude product was diluted with ethyl acetate, washed with saturated NAHCO3 (aq.) and dried over MgSO4. Solvent evaporation afforded tert-butyl (S)-1-[(R)-2-hydroxypropylamino]propan-2-ylcarbamate] in 98.5% yield (3.95 g). It was carried to the next step without further purification.

Workup

  1. customwas hydrogenated at 1 atmosphere overnight
  2. customReaction
  3. filtrationThe reaction mixture was then filtered through a celite bed
  4. customAfter solvent evaporation crude product
  5. additionwas diluted with ethyl acetate
  6. washwashed with saturated NAHCO3 (aq.)
  7. dry with materialdried over MgSO4
  8. customSolvent evaporation

Sources & evidence

ORD record
ord-e7e022c991b343bca0626c5ea527769a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…