Methanol → N-(2-(4-Carbomethoxyphenyl)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

HRID 851497Notes

Reaction equation

HRID 851497 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([C:9]([CH:11]=O)=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([CH3:28])[NH2:27])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16].CO.[BH4-].[Na+]>C1C=CC=CC=1>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:27][CH2:11][CH:9]([OH:10])[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[CH3:28])=[CH:21][CH:20]=1)([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 27832843-(Trifluoromethyl)phenylglyoxalHCID 4311764Sodium borohydrideHCID 15034329Methyl 4-(2-aminopropyl)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 3-trifluoromethylphenyl glyoxal (2.1 g) and 2-(4-carbomethoxyphenyl)-1-methylethanamine (2.0 g) in benzene (150 ml) was refluxed under Dean & Stark conditions for 2 hours. The solvent was replaced with methanol (150 ml), the mixture was cooled in ice and sodium borohydride (4.0 g) was added portionwise. The mixture was stirred at ambient temperature for 3 hours, the solvent was evaporated and the residue was partitioned between water (100 ml) and chloroform (100 ml). The aqueous phase was further extracted with chloroform (100 ml), the combined organic extracts were dried (Mg SO4) and evaporated to an oil which was crystallised from hexane to give the title compound, m.p. 80°-83° as a 25:75 mixture of diastereoisomers. (25% RR,SS:75% RS,SR). τ(CDCl3) 8.95 (3H,d,J=6 Hz) 6.6-7.6 (5H,m), 6.13 (3H,s), 5.3 (1H,m) 2.72 (2H,d,J= 8 Hz), 2.1-2.5 (4H,m), 1.92 (2H,d,J=8 Hz).

Workup

  1. temperaturewas refluxed under Dean & Stark conditions for 2 hours
  2. temperaturethe mixture was cooled in ice
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between water (100 ml) and chloroform (100 ml)
  5. extractionThe aqueous phase was further extracted with chloroform (100 ml)
  6. dry with materialthe combined organic extracts were dried (Mg SO4)
  7. customevaporated to an oil which
  8. customwas crystallised from hexane

Sources & evidence

ORD record
ord-1454560463df46b68675d4c13ef28c92
Source dataset
uspto-grants-1983_05
Patent number
US04385066

Reaction notes

Loading…