HCID 68081227, compound → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

HRID 595805Notes

Reaction equation

HRID 595805 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68081227HCID 68081227, compound

Product 1

HCID 49839963tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylateYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of tert-butyl 6-amino-5′,6′-dihydro-[3,4′-bipyridine]-1′(2′H)-carboxylate (560 mg, 2.03 mmol), 5% Pd/C (1082 mg, 0.5 mmol) in methanol (30 mL) was purged with nitrogen for 2 min. The reaction mixture was stirred under hydrogen at ambient temperature for 16 h. The reaction mixture was diluted with dichloromethane (50 mL) and was filtered through Celite pad. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel (ISCO) eluting with 0-90% ethyl acetate in heptane to give tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate (180 mg, 31.9%) as yellow color solid. LCMS (m/z): 278 (MH+), 0.57 min.

Workup

  1. customwas purged with nitrogen for 2 min
  2. additionThe reaction mixture was diluted with dichloromethane (50 mL)
  3. filtrationwas filtered through Celite pad
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash column chromatography on silica gel (ISCO)
  6. washeluting with 0-90% ethyl acetate in heptane

Sources & evidence

ORD record
ord-2912efda56224b4a85abd2d332c1b767
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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