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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

HRID 132879
Notes
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Reaction equation

HRID 132879 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 692227422-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 692237937-Amino-2-[(3r)-3-[(tert-butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst
HCID 887
Methanol
Solvent

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

  1. customThe reaction flask was purged
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07388019B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes