Reaktion #1956943

Reaktionsgleichung

ester

(±)-Methyl{(2R*,4S*)-1-[(1S*)-1-(4-iodophenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

→

title compound

(±)-{(2S*,4R*)-1-[(1R*)-1-(4-Iodophenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure
2. 2
   Sonstigethe residue partitioned between DCM and 2M HCl
3. 3
   EinengenThe DCM layer was concentrated under reduced pressure
4. 4
   Sonstigeto give the crude product, which
5. 5
   Sonstigewas purified by flash chromatography (silica, 3% MeOH in DCM)

Vorschrift

The ester from Step 1 (50 mg, 0.085 mmol) was stirred in MeOH (1 ml) at RT for 3 d. The reaction mixture was concentrated under reduced pressure and the residue partitioned between DCM and 2M HCl. The DCM layer was concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (silica, 3% MeOH in DCM) to give the title compound, 28 mg (57%). 1H NMR (500 MHz, CDCl3) δ (ppm) 0.58-0.66 (1H, m), 0.81-0.83 (6H, m), 0.86-0.95 (1H, m), 1.14 (1H, dq, J 3.8, 12.1), 1.34 (1H, q, J 12.1), 1.42 (1H, septet, J 6.5), 1.74-1.76 (3H, m), 1.84 (1H, br, d, J 12.7), 2.16-2.29 (2H, m), 2.33 (1H, dt, J 2.2, 12.1), 2.69 (1H, td, J 3.6, 12.1), 3.35 (1H, dd, J 5.1, 9.9), 3.72 (1H, dd, J 2.5, 10.9), 6.98 (2H, d, J 8.1), 7.54 (2H, br, d, J 7.45), 7.59-7.63 (4H, m); M/Z (ES+) 574 (M+H).

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