Dichloromethane → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

HRID 402950Notes

Reaction equation

HRID 402950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 49840377tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 49839963tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitro-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (3 g, 9.84 mmol) in CH3OH: DCM (40 mL, v/v=3:1) was added Pd/C (600 mg) and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. TLC showed a complete reaction. The solution was filtered and the resulting filtrate was evaporated to dryness to give the crude product, which used directly in the next step (2.6 g, 96%). 1H NMR (300 MHz, CDCl3): δ 7.89 (d, J=2.4 Hz, 1H), 7.26 (dd, J=8.4, 2.4 Hz, 1H), 6.46 (d, J=8.4 Hz, 1H), 4.36 (bs, 2H), 4.23-4.19 (m, 2H), 2.81-2.73 (m, 2H), 2.58-2.47 (m, 1H), 1.78-1.73 (m, 2H), 1.61-1.51 (m, 2H), 1.47 (s, 9H).

Workup

  1. customa complete reaction
  2. filtrationThe solution was filtered
  3. customthe resulting filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-e7ce5f4e395e44b78eeb083984260135
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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