Acetic Acid → 1-(4-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanone

HRID 410273Notes

Reaction equation

HRID 410273 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.C(O)(=O)C>C1COCC1.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[C:7]([CH:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:16])[CH3:15])[CH2:12][CH2:13]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 493570RiboflavinHCID 593269651-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

Product 1

HCID 585478341-(4-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.14 g, 0.65 mmol), palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet, degussa type e101 ne/w (91 mg, 0.13 mmol) and acetic acid, glacial (19 uL, 0.32 mmol) were suspended in THF (13 mL) in a pressure tube. The reaction mixture was hydrogenated at 50 psi for 5 h then filtered through a pad of celite and washed with THF. The filtrate was concentrated to give 1-(4-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone as clear oil.

Workup

  1. filtrationthen filtered through a pad of celite
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-31e37c1432794911844449e31eba9a59
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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