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Triphenylphosphine → 6-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one

HRID 496431
Notes
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Reaction equation

HRID 496431 reaction equation
[OH:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[N:16]1([CH2:21][C@H:22](O)[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][N:18]=[CH:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CO.C(Cl)Cl>[N:16]1([CH2:21][C@@H:22]([O:1][C:2]2[C:3]([N+:13]([O-:15])=[O:14])=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][N:18]=[CH:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 123928306-Hydroxy-5-nitro-3,4-dihydronaphthalen-1(2H)-oneHCID 60029931(R)-1-imidazol-1-ylmethyl-2-methyl-propanol

Product 1

HCID 697352806-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-oneYield 69.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 6-hydroxy-5-nitro-1-tetralone (0.888 g, 4.29 mmol) in dry THF (10 mL) was added (R)-1-imidazol-1-ylmethyl-2-methyl-propanol (0.737 g, 4.78 mmol) followed by triphenylphospine (1.26 g, 4.78 mmol). After approximately 10 min, diethylazodicarboxylate (0.75 mL, 4.78 mmol) was added slowly. The reaction was allowed to stir at RT for 2 days. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography (SiO2, 20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a foam (1.02 g, 2.97 mmol, 69%). The structure was confirmed by NMR and mass spectrometry. MS m/z 344 (M++H). 2. 5-Amino-6-((S)-1-imidazol-1-ylmethyl-2-methyl-propoxy)-3,4-dihydro-2H-naphthalen-1-one

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography (SiO2, 20% acetone/CH2Cl2

Sources & evidence

ORD record
ord-7b908bd77cb24f70bebf8b93d49664ea
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06943183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes