(NZ)-N-[(4S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1-ylidene]hydroxylamine → (1R,4S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)/[C:12](=[N:19]\O)/[C:11]([CH3:22])([CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH2:19])[C:11]([CH3:22])([CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 60 (30 mg, 0.089 mmol) in acetic acid (3 mL) was added palladium on charcoal (30 mg, 5%). The mixture was then stirred under hydrogen (1 atm) for 1 h. The catalyst was filtrated away through a pad of Celite. The filtrate was concentrated. The resultant residue was purified by chiral OJ column (ethanol/methanol/hexane/DEA=3:2:95:0.1) to give 59 (12.5 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=8.0 Hz, 1 H), 7.44-7.38 (m, 2 H), 7.38-7.24 (m, 2 H), 6.81 (d, J=7.6 Hz, 1 H), 7.03 (dd, J=1.6, 8.0 Hz, 1 H), 4.28 (dd, J=4.4, 12.4 Hz, 1 H), 2.19 (dd, J=13.6, 12.4 Hz, 1 H), 2.06 (dd, J=13.6, 4.4 Hz, 1 H), 1.58 (s, 1 H), 1.27 (s, 6 H); 13C NMR (100 MHz, CDCl3) δ 145.39, 144.92, 133.53, 133.01, 133.68, 131.19, 131.09, 131.01, 129.24, 128.51, 128.31
Workup
- filtrationThe catalyst was filtrated away through a pad of Celite
- concentrationThe filtrate was concentrated
- customThe resultant residue was purified by chiral OJ column (ethanol/methanol/hexane/DEA=3:2:95:0.1)
Sources & evidence
- ORD record
- ord-f51c110adad549cca43385aeeaac08bc
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053603B2
Reaction notes
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