4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2363813Notes

Reaction equation

HRID 2363813 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[C:16]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[C:16]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 866868854-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866868864-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl esterYield 62.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (0.09 g) was added to a deoxygenated solution of 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (which may be prepared as described above; 0.64 g, 1.6 mmol) in ethanol (30 mL) in a Parr shaker vessel. The mixture was hydrogenated at 60 psi for 16 h and then filtered through a pad of celite. The celite was washed with ethanol (2×5 mL) and the combined filtrates were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100-200 mesh), using 20% ethyl acetate/hexanes as eluent, to give 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.40 g, 62%) as a sticky colorless solid. MS cald. for C23H29FNO4 [(M+H)+] 402, obsd. 402.4.

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe celite was washed with ethanol (2×5 mL)
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (100-200 mesh)

Sources & evidence

ORD record
ord-7e7138ce7e31482580b94871cc909802
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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