2-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline → 7-Amino-2-[(3r)-3-[(tert-butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])[CH2:10][C:11]([N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([N+:23]([O-])=O)=[CH:18][CH:19]=2)[CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:23][C:17]1[CH:16]=[C:15]2[C:20]([CH2:21][CH2:22][N:13]([C:11](=[O:12])[CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[CH2:14]2)=[CH:19][CH:18]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To the product (0.43 g) from Step A above in 4 mL of methanol was added 20% palladium hydroxide on carbon (Pearlman's catalyst, 0.04 g). The reaction was placed under a balloon of hydrogen and allowed to stir at room temperature overnight. The reaction flask was purged, the mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel; 55% ethyl acetate/hexanes) to afford the title compound. LC/MS: 328 (M−100).
Workup
- customThe reaction flask was purged
- filtrationthe mixture was filtered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (silica gel; 55% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-b6548eeb2358482aa07ceb41958a2bfb
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07388019B2
Reaction notes
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