methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate → methyl (4S,5R)-5-(3, 4-dihydroxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate

HRID 343998Notes

Reaction equation

HRID 343998 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C@H:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:25][C@@H:24]2[C:34]([O:36][CH3:37])=[O:35])[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)(C)C>[OH:8][C:9]1[CH:10]=[C:11]([C@H:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:25][C@@H:24]2[C:34]([O:36][CH3:37])=[O:35])[CH:12]=[CH:13][C:14]=1[OH:15]

Participants

5

Reactant 2

HCID 56982455methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 56997612methyl (4S,5R)-5-(3, 4-dihydroxyphenyl)-2-phenyl-2-oxazoline-4-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate (494 mg, 1.00 mmol), 5%-palladium-carbon (64 mg) and isopropanol (5 g) was reduced with hydrogen at room temperature under atmospheric pressure for 15 hours. The reaction mixture was filtered and then the filtrate was concentrated under reduced pressure. The residue was treated with silica gel chromatography to obtain 263 mg (0.84 mmol, yield: 84%) of methyl (4S,5R)-5-(3, 4-dihydroxyphenyl)-2-phenyl-2-oxazoline-4-carboxylate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was treated with silica gel chromatography

Sources & evidence

ORD record
ord-bbdcedd7f0314433ae2532fa1ee3cb14
Source dataset
uspto-grants-1999_01
Patent number
US05864041

Reaction notes

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