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 1599184노트

반응식

HRID 1599184 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 3776Isopropanol용매

실험 절차

A mixture of methyl (4S,5R)-5-(3,4-dibenzyloxyphenyl)-2-phenyl-2-oxazoline4-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.

후처리

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

출처 및 근거

ORD 기록
ord-35143b52aa6e4d70b7c905c83afbe44f
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739387

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