3-(Trifluoromethyl)benzaldehyde → (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine

HRID 322576

Reaction equation

HRID 322576 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C1C=C(C=CC=1)C=O.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C@H:36]([NH2:38])[CH3:37])[CH:33]=[CH:34][CH:35]=1.C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C@H:11]([NH:38][C@@H:36]([C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([O:29][CH3:28])[CH:31]=2)[CH3:37])[CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 133390594-[3-(Trifluoromethyl)phenyl]butan-2-one

Product 1

HCID 9819839(R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

In a similar fashion an equal molar amount of 4-(3-trifluoromethylphenyl)-2-butanone, prepared from m-trifluoromethylbezaldehyde, (R)-1-(3-methoxyphenyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 21Y [m/z (rel. int.) 351 (M+, 2), 336 (18), 216 (4), 202 (3), 178 (45), 135 (100), 105 (13), 91(9), 77 (8)] and (S,R-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 21X.

Workup

  1. additionwere mixed

Sources & evidence

ORD record
ord-c3a3e72caf154fd8a3d4a8f4f0c8ae1a
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Linked notes

Loading…