HCID 86634569, compound → HCID 57878516, compound

HRID 1515359Notes

Reaction equation

HRID 1515359 reaction equation
[CH3:1][C:2](=[CH2:34])[C:3]#[C:4][C@@H:5]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:15][C@H:14]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>CO.[Ni]>[CH3:1][CH:2]([CH3:34])[CH2:3][CH2:4][C@@H:5]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:15][C@H:14]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=1)[CH2:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 86634569HCID 86634569, compound

Product 1

HCID 57878516HCID 57878516, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-b385e770e67a47488bef444cd659cb56
Source dataset
uspto-grants-2012_07
Patent number
US08222418B2

Reaction notes

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