Water → (S,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamIne

HRID 322573Notes

Reaction equation

HRID 322573 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12](=O)[CH3:13])[CH:7]=[CH:8][CH:9]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C@H:25]([NH2:27])[CH3:26])[CH:22]=[CH:23][CH:24]=1.C([BH3-])#N.[Na+].O>C(OCC)C.C(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C@H:12]([NH:27][C@H:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH3:17])[CH:20]=2)[CH3:26])[CH3:13])[CH:7]=[CH:8][CH:9]=1.[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C@H:12]([NH:27][C@@H:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH3:17])[CH:20]=2)[CH3:26])[CH3:13])[CH:7]=[CH:8][CH:9]=1

Participants

10

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 235060554-(3-Trifluoromethoxyphenyl)-2-butanone

Product 2

HCID 53962620(S,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamIneHCID 53962621(R,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A solution of 4(3-trifluoromethoxyphenyl)-2-butanone (2.32 g, 10 mmol), (R)-1-(3-methoxyphenyl)ethylamine (1.51 g, 10 mmol), and titanium (IV) isopropoxide (3.55 g, 12.5 mmol) were stirred 4 hr at rt. The reaction mixture was then treated with a solution (10 ml of 1 M) of ethanolic sodium cyanoborohydride (10 mmol) and stirred 16 hr at rt. The reaction was diluted with diethyl ether (50 ml) and treated with water (0.72 ml, 40 mmol). After mixing thoroughly the solution was centrifuged and the ether layer decanted and concentrated to a oily solid. The solid was suspended in diethyl ether, filtered through 0.45 μM CR PTFE Acrodisc and concentrated to give a clear oil. Repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded the two diasteriomers, (S,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamIne, 22Z [m/z (rel. int.) 367 (M+, 3), 352 (20), 232 (4), 178 (47), 135 (100), 105 (14), 91 (10), 77 (11)] and (R,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 23A; m/z (rel. int.) 367 (M+, 3), 352 (19), 232 (7), 178 (43), 135 (100), 105 (19), 91 (10), 77 (11).

Workup

  1. additionAfter mixing thoroughly the solution
  2. customthe ether layer decanted
  3. concentrationconcentrated to a oily solid
  4. filtrationfiltered through 0.45 μM CR PTFE Acrodisc
  5. concentrationconcentrated
  6. customto give a clear oil

Sources & evidence

ORD record
ord-8d6815e45ec44159a99f8a0ecfb5dcdf
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Reaction notes

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