HCID 59453009, compound → HCID 59452872, compound

HRID 419391Notes

Reaction equation

HRID 419391 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:27][CH2:26][N:25]4[C@H:20]([CH2:21][O:22][CH2:23][CH2:24]4)[CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCOC(C)=O.[Pd]>[CH2:21]1[C@@H:20]2[CH2:19][N:18]([CH:15]3[CH2:14][CH2:13][N:12]([C:5]4[CH:6]=[CH:7][C:8]([NH2:9])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:17][CH2:16]3)[CH2:27][CH2:26][N:25]2[CH2:24][CH2:23][O:22]1

Participants

4

Reactant 1

HCID 59453009HCID 59453009, compound

Product 1

HCID 59452872HCID 59452872, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To (9aS)-8-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}octahydropyrazino[2,1-c][1,4]-oxazine (0.516 g, 1.35 mmol) in EtOAc (50 mL) was added Pd on carbon. The mixture was stirred under H2 (1 atm) overnight. The mixture was filtered through Celite® to provide the title compound of step I (0.417 g, 1.20 mmol, 89%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.56 (m, 2H), 1.77-1.88 (m, 2H), 2.10-2.22 (m, 2H), 2.42 (s, 4H), 2.48 (s, 5H), 2.58 (d, J=12.1 Hz, 1H), 2.69 (d, J=9.9 Hz, 1H), 3.04 (t, J=10.4 Hz, 1H), 3.37-3.47 (m, 3H), 3.59 (d, J=11.4 Hz, 1H), 3.66-3.73 (m, 5H), 6.25 (dd, J=8.3, 2.1 Hz, 1H), 6.43-6.51 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite®

Sources & evidence

ORD record
ord-9ed097f66d974a629e4b31b0f83276e1
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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