Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate → (2S,3R)-3-amino-1-[(tripropan-2-ylsilyl)oxy]butan-2-ol

HRID 1964645Notes

Reaction equation

HRID 1964645 reaction equation
C(OC(=O)[NH:10][C@@H:11]([C@H:13]([OH:26])[CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH3:12])C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH2:10][C@H:11]([CH3:12])[C@H:13]([OH:26])[CH2:14][O:15][Si:16]([CH:17]([CH3:19])[CH3:18])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 86649570Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate

Product 1

HCID 86649571(2S,3R)-3-amino-1-[(tripropan-2-ylsilyl)oxy]butan-2-olYield 108.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate (3.70 g, 9.35 mmol) synthesized in Example (89d) was dissolved in ethanol (30 mL), and palladium carbon (1.00 g) was added, followed by stirring at room temperature for 8 hours under hydrogen atmosphere. After Celite filtration, the solvent was distilled off under reduced pressure to afford the desired compound (2.65 g, yield ˜100%) as a pale yellow liquid.

Workup

  1. filtrationAfter Celite filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2879c3db6311473eba7dd9a2b4fa8a57
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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