HCID 57211727, compound → HCID 57151220, compound

HRID 1815554Notes

Reaction equation

HRID 1815554 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][C@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:15]([OH:22])[CH2:16][NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[OH:22][C@H:15]([CH2:16][NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 57211727HCID 57211727, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57151220HCID 57151220, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-(isobutylamino)propylcarbamate (0.5 g, 1.1 mmol) in anhydrous tetrahydrofuran (12 mL) was added 0.5 g of palladium (on charcoal, 10% Pd, Degussa type). The mixture was stirred under an atmospheric pressure of hydrogen for 12 hours. The catalyst was filtered and the solvent was removed under reduced pressure resulting in 0.4 g (98%) of the title compound. 1H-NMR (CDCl3): δ 0.92 (6H,dd), 1.35 (9H,s), 1.83 (1H,m), 2.44-2.55 (2H,m), 2.73-2.85 (4H,m), 3.49 (1H,m), 3.70-3.79 (1H,m,b), 4.66 (1H,d), 6.72 (2H,d), 7.05 (2H,d).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de98f6d5ac4147d1a51662efbb27bdc4
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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