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 909585Notes

Reaction equation

HRID 909585 reaction equation
[OH:1][C@H:2]([CH2:16][O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[C@H:3]([NH:5]C(=O)OCC1C=CC=CC=1)[CH3:4]>C(O)C.[C].[Pd]>[NH2:5][C@H:3]([CH3:4])[C@H:2]([OH:1])[CH2:16][O:17][Si:18]([CH:19]([CH3:21])[CH3:20])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23]

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-b4444e0c5d734e8a9f4f5a04c037d940
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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