HCID 45100915, compound → HCID 45100916, compound

HRID 885206Notes

Reaction equation

HRID 885206 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C@@H:13]([CH2:21][CH3:22])[CH2:14][C@H:15]1[CH2:19][O:18][C:17]([NH2:20])=[N:16]1)C1C=CC=CC=1>CO.[Pd]>[NH2:20][C:17]1[O:18][CH2:19][C@H:15]([CH2:14][C@@H:13]([O:12][C:11]2[CH:10]=[C:9]([OH:8])[CH:25]=[CH:24][CH:23]=2)[CH2:21][CH3:22])[N:16]=1

Participants

4

Reactant 1

HCID 45100915HCID 45100915, compound

Product 1

HCID 45100916HCID 45100916, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-4-[(S)-2-(3-benzyloxy-phenoxy)-butyl]-4,5-dihydro-oxazol-2-ylamine (60 mg) in methanol (3 ml) at room temperature was added 10% palladium on charcoal (19 mg). The mixture was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 1 h. The catalyst was removed by filtration through decalite, washing with methanol and with dichloromethane, and the filtrate was concentrated in vacuo to yield 3-[(S)-1-((S)-2-amino-4,5-dihydro-oxazol-4-ylmethyl)-propoxy]-phenol as a white solid (44 mg, quant.); MS (ISP): 251.2 ([M+H]+).

Workup

  1. customThe catalyst was removed by filtration through decalite
  2. washwashing with methanol and with dichloromethane
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8747473be81345cfad983e441481355c
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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