2-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-ol → N-(2-(4-Carbomethoxyphenyl)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

HRID 851498Notes

Reaction equation

HRID 851498 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[OH:15][CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[CH2:17][NH2:18].[BH4-].[Na+]>C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:18][CH2:17][CH:16]([OH:15])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=2)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 4311764Sodium borohydrideHCID 11137970Methyl 4-(2-oxopropyl)benzoate

Product 1

HCID 14823030N-(2-(4-Carbomethoxyphenyl)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-carbomethoxyphenyl)propan-2-one (2.25 g) and 2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (2.4 g) in benzene (100 ml) was refluxed under Dean & Stark conditions for 2 hours. The resulting adduct was reduced with sodium borohydride and the product was isolated as in part 1). Crystallisation from ether gave the title compound m.p. 73°-88° as a 50:50 mixture of diastereoisomers. Recrystallisation of this mixture from ethyl acetate gave a sample m.p. 82°-85°, predominantly the RS,SR diastereoisomer (12:88).

Workup

  1. temperaturewas refluxed under Dean & Stark conditions for 2 hours
  2. customthe product was isolated as in part 1)
  3. customCrystallisation from ether

Sources & evidence

ORD record
ord-c60e30ad13724002bd9d88dac82d4711
Source dataset
uspto-grants-1983_05
Patent number
US04385066

Reaction notes

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