(R)-N-Methyl-1-[3,5-bis(trifluoromethyl)phenyl]ethylamine synthesis

10synthesis methods

Product Name:(R)-N-Methyl-1-[3,5-bis(trifluoromethyl)phenyl]ethylamine
CAS Number:334477-60-0
Molecular formula:C11H11F6N
Molecular Weight:271.2

Benzenemethanamine, N,α-dimethyl-N-[(1S)-1-phenylethyl]-3,5-bis(trifluoromethyl)-, (αR)-

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(R)-N-Methyl-1-[3,5-bis(trifluoromethyl)phenyl]ethylamine

334477-60-0
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$95.00/250mg

Yield:334477-60-0 92%

Reaction Conditions:

with hydrogen;5%-palladium/activated carbon in methanol at 60; under 3750.38 Torr; for 17.5 h;

Steps:

11.b Step (b), hydrogenolysis

Step (b), hydrogenolysis. To 2.4 ml of methanol, 0.90 g (2.40 mmol, 1eq.) of the above purified product of the optically active tertiary amine and 18.0 mg (0.05wt% Pd) of a palladium catalyst (having 5% palladium carried on an activated carbon containing 50wt% of water) were added. The hydrogen pressure was adjusted to 0.5 MPa, and the stirring was conducted at 60°C for 17.5 hr. After the reaction, the reaction liquid was filtrated using a filtration aid (CELITE (trade name)), concentrated, and vacuum-dried, thereby obtaining 0.60g of a crude product of an optically active (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethylamine N-monomethyl, represented by the following formula. The yield was 92%. The above crude product was found by chiral gas chromatography to have a conversion of 100% and an enantiomeric excess of 100 %ee. In terms of severing position selectivity whether the N-C* bond is severed at the broken line "a" to produce a compound A or at the broken line "b" to produce a compound B (i.e., the above optically active (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethylamine N-monomethyl) in the above formula 11, the above crude product was found by chiral gas chromatography to contain 1 part by mole of the compound A and 99 parts by mole of the compound B. 1H-NMR(TMS, CDCl3), δ ppm: 1.38 (d, 6.4 Hz, 3H), 1.45 (br, 1H), 2.30 (s,3H), 3.81 (q, 6.4 Hz, 1H), 7.75 (Ar-H, 1H), 7.80 (Ar-H, 2H)

References:

WO2004/22521,2004,A1 Location in patent:Page 57-58