Ammonium formate → Tert-butyl 6-(4-amino-4-methylpiperidin-1-yl)pyridine-3-carboxylate

HRID 855848Notes

Reaction equation

HRID 855848 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][C:17]([NH:21]C(OCC3C=CC=CC=3)=O)([CH3:20])[CH2:16][CH2:15]2)=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)(C)C.CO.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][C:17]([NH2:21])([CH3:20])[CH2:16][CH2:15]2)=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 667571374-benzyloxycarbonylamino-4methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-5'-carboxylic acid tert-butyl ester

Product 1

HCID 66756953Tert-butyl 6-(4-amino-4-methylpiperidin-1-yl)pyridine-3-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-benzyloxycarbonylamino-4-methyl-3,4,5,6-tetrahydro-2H-(1,2′)bipyridinyl-5′-carboxylic acid tert-butyl ester (0.29 g, 0.68 mmol) in isopropanol, methanol and ethyl acetate (1:1:1, 5.0 mL) at room temperature was added ammonium formate (0.25 g, 1.07 mmol) and 10% Pd/C (25 mg) under nitrogen. The reaction mixture was stirred at 80° C. for 30 minutes, cooled, filtered through Celite, and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 292 (M+1)+; 1H NMR (300 MHz, methanol-d4) δ ppm 8.61(d, 1H), 7.95 (d, d 1H), 6.79 (d, 1H), 4.80 (s, 2H), 3.85-3.79 (m, 2H), 3.66-3.60 (m, 2H), 1.67-1.59 (m, 4H), 1.58 (s, 9H), 1.23 (s, 3H).

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8af06383ac9f464483bd7d6a3a82974e
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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