Hydrazine hydrate (1:1) → HCID 66893657, compound

HRID 1162027Notes

Reaction equation

HRID 1162027 reaction equation
[F:1][C@H:2]1[C@@H:7]([O:8][C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([N+:18]([O-])=O)[CH:10]=2)[CH2:6][CH2:5][N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:3]1.O.NN>C1COCC1.C(O)C.[Ni]>[NH2:18][C:11]1[CH:10]=[C:9]([O:8][C@H:7]2[CH2:6][CH2:5][N:4]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:3][C@H:2]2[F:1])[C:17]2[O:16][CH:15]=[CH:14][C:13]=2[CH:12]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66894299HCID 66894299, compound2×

Product 1

HCID 66893657HCID 66893657, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl cis-3-fluoro-4-[(5-nitro-1-benzofuran-7-yl)oxy]piperidine-1-carboxylate (200 mg, 0.526 mmol; Intermediate 50) dissolved in THF (10 mL) and ethanol (40 mL), was added Raney-nickel (as a slurry in ethanol) and hydrazine hydrate (0.2 mL). The mixture was stirred at room temperature for 30 min and then filtered through Celite and evaporated. The residue was re-dissolved in toluene and evaporated again. This material was used directly in the subsequent experiment.

Workup

  1. filtrationfiltered through Celite
  2. customevaporated
  3. dissolutionThe residue was re-dissolved in toluene
  4. customevaporated again

Sources & evidence

ORD record
ord-f9366e473d6f4089bf6145b4fa0c4682
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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