HCID 57526932, compound → HCID 57526939, compound

HRID 1452669Notes

Reaction equation

HRID 1452669 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)=[CH:4][C:3]=1[N+:21]([O-])=O.[H][H]>C(OCC)(=O)C.CO.[Pd]>[C:17]([O:16][C:14]([N:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH2:21])[CH:4]=2)[CH2:13][CH2:12]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 2

HCID 57526932HCID 57526932, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57526939HCID 57526939, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (2.35 g, 8.85 mmol) and 10% Pd/C (400 mg) in ethyl acetate (40.0 mL) and methanol (10.0 mL) was hydrogenated at room temperature for 72 hours using hydrogen bomb (200 psi). The reaction mixture was filtered through Celite and the Celite was washed with EtOAc/MeOH (1:1, 3×50 mL). The filtrate was concentrated in vacuo to afford tert-butyl-4-(3-amino-4-fluorophenyl)-1-piperidinecarboxylate (2.10 g, 98.0%): 1H NMR (400 MHz, CDCl3) δ 6.96-6.76 (m, 1H), 6.67-6.54 (m, 1H), 6.54-6.40 (m, 1H), 4.38-4.09 (br, 2H), 4.09-3.58 (br, 2H), 2.87-2.62 (m, 2H), 2.60-2.39 (m, 1H), 1.85-1.65 (m, 2H), 1.64-1.40 (m, 2H), 1.48 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe Celite was washed with EtOAc/MeOH (1:1, 3×50 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4f555ef0e1f48f18515ad494ea8be05
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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