Acetic Acid → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)amine
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]=[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][NH:13][CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 96 (1.42 g, 4.07 mmol) in anhydrous dichloroethane (10 mL) were sequentially added acetic acid (267 mg, 4.48 mmol) and NaBH(OAc)3 (1.12 g, 5.29 mmol) under N2. The reaction was stirred at room temperature for 2 hours before it was quenched by slow addition of water (100 mL). The mixture was extracted with dichloromethane (100 mL) and the organic layer was sequentially washed with water (100 mL), saturated aq. NaHCO3 (100 mL), and water (100 mL). The residue, from drying (Na2SO4) and concentrating the organic layer, was chromatographed on silica gel (EtOAc to 5:1 EtOAc/CH3OH) to yield 97 as a brown oil (755 mg, 53%).
Workup
- customwas quenched by slow addition of water (100 mL)
- extractionThe mixture was extracted with dichloromethane (100 mL)
- washthe organic layer was sequentially washed with water (100 mL), saturated aq. NaHCO3 (100 mL), and water (100 mL)
- dry with materialThe residue, from drying (Na2SO4)
- concentrationconcentrating the organic layer
- customwas chromatographed on silica gel (EtOAc to 5:1 EtOAc/CH3OH)
Sources & evidence
- ORD record
- ord-975ab0393c2142cd90033175a94dbf65
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265122B2
Reaction notes
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