HCID 16225490, compound → HCID 16225684, compound

HRID 334328Notes

Reaction equation

HRID 334328 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:9][CH2:10][C:11]([N:13]2[CH2:26][CH2:25][C:16]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17]3)[CH2:15][CH2:14]2)=[O:12])=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[CH2:9][CH2:10][C:11]([N:13]2[CH2:26][CH2:25][C:16]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 16225490HCID 16225490, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16225684HCID 16225684, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.50 g (1.13 mmol) of 1-[4,4-bis(4-fluorophenyl)but-3-enoyl]-spiro[piperidine-4,1′-indene] (33) was dissolved in 20 mL of methanol under nitrogen atmosphere and then 200 mg of palladium/Charcoal (5%, Aldrich) was added. The nitrogen atmosphere was replaced with hydrogen gas. The resulting mixture was stirred at room temperature for 6 hours and filtered through a pad of celite. The methanol solution (200 mL) was concentrated and the resulting residue purified by column chromatography using a gradient of ethyl acetate/hexane as eluent to give 0.5 g of the title compound 35. MS: m/z 445. 1H NMR (CDCl3): δ 7.24-7.17 (m, 7H), 7.10-7.07 (m, 1H), 7.02-6.95 (m, 4H), 4.67-4.57 (m, 1H), 4.04-3.93 (m, 1H), 3.68-3.58 (m, 1H), 3.18-3.06 (m, 1H), 2.98-2.85 (m, 2H), 2.82-2.71 (m, 1H), 2.44-2.33 (m, 2H), 2.33-2.24 (m, 2H), 2.14-1.99 (m, 2H), 1.82-1.61 (m, 2H), 1.61-1.48 (m, 3H).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe methanol solution (200 mL) was concentrated
  3. customthe resulting residue purified by column chromatography

Sources & evidence

ORD record
ord-6d0c7fd931fd4333a52808e793f85da5
Source dataset
uspto-grants-2014_11
Patent number
US08883816B2

Reaction notes

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