tert-butyl 4-(2-fluoro-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-2-fluorophenyl)piperidine-1-carboxylate

HRID 1778985Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1>CCOC(C)=O.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of tert-butyl 4-(2-fluoro-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (A27) (0.391 g, 1.20 mmol) in EtOAc (10 mL) was added 10% Pd/C (0.118 g) in EtOAc (1 mL) and the resulting suspension was stirred at 30° C. under a hydrogen atmosphere for 16 hours. The resulting mixture was filtered through Celite and the filtrate concentrated under reduced pressure to give the title compound A28 (0.339 g, 96%); 1H NMR (400 MHz, CDCl3) δ 6.94 (dd, J=8.3 Hz, 1H), 6.41 (dd, J=8.2, 2.4 Hz, 1H), 6.36 (dd, J=12.1, 2.3 Hz, 1H), 4.21 (brs, 2H), 3.65 (s, 2H), 2.84 (m, 3H), 1.75 (bd, J=13.3 Hz, 2H), 1.47 (s, 9H).

Workup

filtrationThe resulting mixture was filtered through Celite
concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record: ord-bac9a547b0064941aac8071a6232e24f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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