5-[3'-(t-Butoxycarbonylamino)propyloxy]-1-hydroxy-8-nitro-1,2,3,4-tetrahydronaphthalene → 5-[3'-(t-Butoxycarbonylamino)propyloxy]-8-nitro-1,2,3,4-tetrahydronaphthalen-1-one
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][CH:18]2[OH:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)(Cl)(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
5-[3'-(t-Butoxycarbonylamino)propyloxy]-1-hydroxy-8-nitro-1,2,3,4-tetrahydronaphthalene (2.46 g) is dissolved in dry methylene chloride (110 ml), and thereto are added molecular sieves 3A (6.73 g) and pyridinium dichlorochromate (1.5 equivalent), and the mixture is refluxed. After the reaction is completed, the mixture is diluted with ether, and the insoluble materials are removed by filtration through a pad of Celite. The filtrate is concentrated, and the residue is purified by silica gel column chromatography to give the title compound (1.87 g) as a colorless powder.
Workup
- temperaturethe mixture is refluxed
- customthe insoluble materials are removed by filtration through a pad of Celite
- concentrationThe filtrate is concentrated
- customthe residue is purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9574c7c5c1d546eabdbb44cc6d8548a7
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05892043
Reaction notes
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