HCID 57526945, compound → HCID 57526936, compound

HRID 1452664Notes

Reaction equation

HRID 1452664 reaction equation
C(OC([NH:11][C:12]1[C:13]([F:32])=[CH:14][C:15]([F:31])=[C:16]([C:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH:23]=2)[CH:17]=1)=O)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:11][C:12]1[C:13]([F:32])=[CH:14][C:15]([F:31])=[C:16]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:19]2)[CH:17]=1

Participants

6

Reactant 2

HCID 57526945HCID 57526945, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57526936HCID 57526936, compoundYield 123.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(5-{[(benzyloxy)carbonyl]amino}-2,4-difluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (1.60 g, 3.60 mmol) and 5% Pd/C (320 mg, 0.100 mmol) in ethyl acetate (25.0 mL) and methanol (25.0 mL) was hydrogenated at room temperature for 72 hours using hydrogen bomb (200 psi). The reaction mixture was filtered through Celite and washed with EtOAc/MeOH (1:1, 3×50 mL). The filtrate was concentrated in vacuo to afford tert-butyl 4-(5-amino-2,4-difluorophenyl)-1-piperidinecarboxylate (1.39 g, 100%). 1H NMR (400 MHz, CDCl3) δ 6.73 (t, 1H, J=10.6 Hz), 6.60-6.54 (dd, 1H, J=7.6, 6.57 Hz), 4.20 (br, 2H), 3.55 (s, 2H), 2.96-2.72 (m, 3H), 1.79-1.71 (m, 2H), 1.58-1.52 (m, 2H), 1.47 (s, 9H); ESMS m/e: 257.3 (M−56).

Workup

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

Sources & evidence

ORD record
ord-c3420374eccd4fab9083f2005479ea90
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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