Reaktion #1602541

Reaktionsgleichung

methyl {(2S,4R)-1-[(1S)-4-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)pent-4-en-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

→

alkane

Methyl {(2S,4R)-1-[(1R)-4-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)pentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed by filtration
2. 2
   Waschenwashing with CH2Cl2
3. 3
   SonstigeThe filtrate was evaporated
4. 4
   Sonstigethe residue was purified by chromatography (silica, 25% Et2O/isohexane)

Vorschrift

A solution of methyl {(2S,4R)-1-[(1S)-4-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)pent-4-en-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (ester intermediate from the preparation of Example 20, 221 mg, 0.46 mmol) in MeOH (10 ml) was hydrogenated over Raney Nickel (500 mg) for 4 hrs at 45 psi. The catalyst was removed by filtration washing with CH2Cl2. The filtrate was evaporated and the residue was purified by chromatography (silica, 25% Et2O/isohexane) to give the alkane (154 mg) as an oil. 1H NMR (360 MHz, CDCl3): δ 0.62-0.70 (1H, m), 0.81-1.03 (10H, m), 1.08-1.95 (12H, m), 2.17-2.31 (4H, m), 2.95 (1H, brd, J 12.0), 3.33 (1H, t, J 11.6), 3.41 (1H, t, J 11.5), 3.58 (1H, d, J 9.0), 3.64 (3H, s), 3.86 (1H, brd, J 10.6), 3.92 (1H, brd, J 11.0), 7.38-7.40 (2H, d, m), 7.53 (2H, d, J 8.1); M/Z (ES+) 484 (MH+).

Quelle