HCID 45102369, compound → HCID 59173144, compound

HRID 885202Notes

Reaction equation

HRID 885202 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[O:12][CH2:13][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][CH2:13][O:12][C:11]2[CH:10]=[C:9]([OH:8])[CH:23]=[CH:22][CH:21]=2)[N:16]=1

Participants

4

Reactant 1

HCID 45102369HCID 45102369, compound

Product 1

HCID 59173144HCID 59173144, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-4-[2-(3-benzyloxy-phenoxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine (0.04 g) at room temperature in methanol (2 ml) under an argon atmosphere was added palladium on charcoal (10%, 15 mg). The mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The catalyst was filtered off, the filtrate was concentrated and purified by column chromatography to give 3-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethoxy]-phenol (0.018 g) as a light yellow oil. MS (ISP): 223.3 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-f664f8de705b4c35bfa8db660c18acb0
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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