Hydrochloric Acid → 1(R)-(3-Chloro-phenyl)-2-[1,1-dimethyl-2-(4-nitro-phenyl)-ethylamino]-ethanol
Reaction equation
[NH2:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.C[Si](C)(C)NC(=O)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C@H:27]1[O:29][CH2:28]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.CO>[Cl:23][C:24]1[CH:25]=[C:26]([C@@H:27]([OH:29])[CH2:28][NH:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[CH:30]=[CH:31][CH:32]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
A solution of 2.2 g of 2-amino-2-methyl-1-(4-nitrophenyl)propane (prepared by the procedures described in J. Milecki, et al. J. Med. Chem., 30, 1563 (1987)) and N-trimethylsilylacetamide (1.6 g) in 2.2 mL DMSO was stirred for 30 min, then (R)-3-chlorostyrene oxide (1.8 g) was added and the resulting solution was stirred at 95° C. for 22 h. The reaction solution was allowed to cool, poured over a mixture of ice (30 g) and 6 N aqueous hydrochloric acid (10 mL). A small portion of MeOH was added to produce a homogenous solution, which was stirred for 30 min. The resulting solution was basified with saturated aqueous sodium carbonate, extracted with ethyl acetate, the organic phase dried (Na2SO4) and concentrated in vacuo to afford 4.3 g of the title compound (I-1a) as an orange oil.
Workup
- temperatureto cool
- customto produce a homogenous solution, which
- stirringwas stirred for 30 min
- extractionextracted with ethyl acetate
- dry with materialthe organic phase dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-16f1c4c9be71468b86d595aa474f30fa
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06939867B2
Reaction notes
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