HCID 22626613, compound → tert-butyl 4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)piperidine-1-carboxylate

HRID 277886Notes

Reaction equation

HRID 277886 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>[Pd].CCOC(C)=O>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:23]=[CH:22][C:21]3[CH2:20][CH2:19][CH2:18][NH:17][C:16]=3[N:15]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 22626613HCID 22626613, compound

Product 1

HCID 11197916tert-butyl 4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-3 (2.6 g, 8.4 mmol), 10% Pd/C (0.52 g), and EtOAc (100 mL) stirred under a hydrogen atmosphere (1 atm) for 20 hrs. The reaction mixture was then filtered through a celite pad and the filtrate concentrated. Flash chromatography (silica, 70% hexanes/EtOAc to EtOAc) gave 4-4 as a colorless oil.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3ef98f033a714bd88adb335cccb14913
Source dataset
uspto-grants-2002_03
Patent number
US06358970B1

Reaction notes

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