tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate → tert-Butyl 4-(pyridin-2-yl)piperidine-1-carboxylate

HRID 1768384Notes

Reaction equation

HRID 1768384 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 16094711tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 11108143tert-Butyl 4-(pyridin-2-yl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Next, 3′,6′-Dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (9.0 g) was hydrogenated using 10% Pd/C dry (900 mg) at 60 psi at room temperature for 1.5 hr to give 8.9 g (99%) of 3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 1.41 (s, 9H), 1.58 (m, 2H), 1.81 (m, 2H), 2.85 (m, 3H), 4.06 (m, 2H), 7.20 (dd, 1H), 7.28 (d, J=9 Hz, 1H), 7.70 (m, 1H), 8.48 (m, 1H).

Workup

  1. customdry (900 mg) at 60 psi at room temperature for 1.5 hr

Sources & evidence

ORD record
ord-0c911bddcd1145b38dfd29a84b2a7b19
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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