Hydrazine → HCID 86609637, compound

HRID 1162021Notes

Reaction equation

HRID 1162021 reaction equation
NN.[C:3]([O:7][C:8](=[O:28])[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([N+:25]([O-])=O)[CH:17]=2)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4]>C1COCC1.C(O)C.[Ni]>[C:3]([O:7][C:8](=[O:28])[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([NH2:25])[CH:17]=2)[CH2:14][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 2

HCID 9321HydrazineHCID 86609636HCID 86609636, compound2×

Product 1

HCID 86609637HCID 86609637, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrazine (1.038 mL, 28 mmol) and raney-nickel (slurry in ethanol; 10 mL) were added to tert-butyl[1-(5-nitro-1-benzofuran-7-yl)piperidine-4-yl]carbamate (1.03 g, 2.85 mmol; Intermediate 48) in a mixture of THF (50 mL) and ethanol (150 mL). The mixture was stirred at room temperature for 16 h, filtered through a pad of Celite and concentrated in vacuo to afford 1.02 g (quantitative) of the title product. HPLC 95%, RT: 1.746 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 1.45 (s, 9H) 1.65-1.69 (m, 2H) 1.72-1.96 (m, 2H) 2.76-2.85 (m, 2H) 3.50-3.54 (m, 1H) 3.76 (d, J=12.62 Hz, 2H) 6.33 (d, J=1.98 Hz, 1H) 6.54 (d, J=1.98 Hz, 1H) 6.60 (d, J=2.23 Hz, 1H) 7.59 (d, J=1.98 Hz, 1H). LC-MS 332 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c421a1f9c0449fdad4d60d9924d54e1
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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