Reaktion #1266041

Reaktionsgleichung

H2O

3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone

methylamine

methanol

sodium borohydride

→

title compound

Ausbeute 62.0%

3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-N-methyl-3-phenylcyclohexanamine trifluoroacetic acid salt

Ausbeute 62.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to room temperature
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   Extraktionthe mixture was extracted with dichloromethane 3 times
5. 5
   EinengenThe combined organic layers were concentrated
6. 6
   Sonstigeresidue was purified by preparative HPLC

Vorschrift

To a solution of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone (10 mg) in methylamine (2.0 M solution in THF, 0.11 mL) at room temperature was added titanium(IV) isopropoxide (0.02 mL) and the resulting solution was heated at 80° C. in a sealed vial for 1.5 h. The solution was cooled to room temperature, 0.1 mL methanol was added followed by sodium borohydride (4.4 mg), and the resulting suspension was stirred at room temperature for 2 h. H2O was added to quench the reaction and the mixture was extracted with dichloromethane 3 times. The combined organic layers were concentrated and residue was purified by preparative HPLC to give the title compound (8 mg, 62% yield). 1H NMR (500 MHz, CD3OD) δ 1.39 (1H, m), 1.56 (1H, m), 1.72 (1H, m), 1.88 (1H, m), 2.14 (1H, m), 2.39 (1H, m), 2.61 (1H, m), 2.70 (3H, d, J=25 Hz), 2.71 (1H, m), 3.44 (1H, d, J=5 Hz), 3.79 (2H, dd, J=10, 60 Hz), 4.49-4.60 (2H, m), 7.21-7.28 (1H, m), 7.33 (1H, t, J=8 Hz), 7.38-7.46 (3H, m), 7.65 (1H, s), 7.72 (1H, s), 7.82 (1H, d, J=10 Hz). HPLC purity (retention time): 95% (2.05 min, method C). MS: 446.49 (MH+).

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