tert-Butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)piperidine-1-carboxylate

HRID 705780Notes

Reaction equation

HRID 705780 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]=2)=[CH:11][C:10]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[CH:11][C:10]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68283496tert-Butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 68282889tert-Butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I53) (0.409 g, 1.04 mmol) and 10% Pd/C (0.043 g) in EtOAc (20 mL) was stirred for 16 hours at room temperature under a H2 atmosphere. The mixture was filtered through celite and the filtrate concentrated under reduced pressure to give the title compound (I54) (0.376 g, 92%) as a white foam; 1H NMR (400 MHz, CDCl3) δ 7.09 (dd, J=8.1, 8.1 Hz, 1H), 6.95 (m, 2H), 4.25 (m, 2H), 2.79 (dd, J=12.0, 12.0 Hz, 2H), 2.65 (m, 1H), 1.82 (m, 2H), 1.43 (s, 18H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-89d97130b9fb4bc1978afe48e59f2c9b
Source dataset
uspto-grants-2015_11
Patent number
US09174946B2

Reaction notes

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