Hydrazine hydrate (1:1) → HCID 54431991, compound

HRID 1830985Notes

Reaction equation

HRID 1830985 reaction equation
O.NN.[CH3:4][C:5]1[C:19]([O:20][CH3:21])=[CH:18][C:8]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:16][OH:17])=[O:10])=[C:7]([N+:22]([O-])=O)[C:6]=1[O:25][CH3:26].[H][H]>CO.[Ni]>[NH2:22][C:7]1[C:6]([O:25][CH3:26])=[C:5]([CH3:4])[C:19]([O:20][CH3:21])=[CH:18][C:8]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17])=[O:10]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 22046687HCID 22046687, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54431991HCID 54431991, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (1.26 g, 39.37 mmol) was added dropwise to a solution of 190 (2.13 g, 6.56 mmol) in methanol (50 mL) gently refluxing over Raney nickel (1 g, slurry). The resulting vigorous evolution of hydrogen gas subsided after approximately 10 minutes and the reaction was deemed to be complete by TLC after 2 h. The reaction mixture was filtered through celite and the solvent evaporated. Distilled water (100 mL) was added to the residue, and the aqueous mixture was extracted with EtOAc (3×100 mL) and the combined organic phase washed with H2O (3×100 mL) and brine (3×100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent afforded the product as a brown glass (191) (1.91 g, 6.50 mmol) which was protected directly as the troc-carbamate.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent evaporated
  3. additionDistilled water (100 mL) was added to the residue
  4. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  5. washthe combined organic phase washed with H2O (3×100 mL) and brine (3×100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2247114751294574bfd7fbd047b5b52e
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

Loading…