Hydrazine hydrate (1:1) → HCID 70207479, compound

HRID 1378388Notes

Reaction equation

HRID 1378388 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]([F:19])([F:18])[F:17])[C@H:13]([CH2:20][N:21]2C(=O)C3=CC=CC=C3C2=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]([F:19])([F:17])[F:18])[C@H:13]([CH2:20][NH2:21])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70204323HCID 70204323, compound

Product 1

HCID 70207479HCID 70207479, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol, is dissolved 9.33 g (21.6 mmol) of trans-1-benzyloxycarbonyl-3-phthalimidomethyl-4-trifluoromethylpyrrolidine. To the above solution, is added 2.1 ml (43.2 mmol) of hydrazine monohydrate, and the mixture is stirred at room temperature for 12 hours. The resulting precipitate is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with water. The washed solution is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (elusion solvent; chloroform/methanol (100/2→100/5)) to give 5.89 g of the objective substance as a yellow oily matter (yield 90.3%).

Workup

  1. customThe resulting precipitate is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe washed solution is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (elusion solvent; chloroform/methanol (100/2→100/5))
  8. customto give 5.89 g of the objective substance as a yellow oily matter (yield 90.3%)

Sources & evidence

ORD record
ord-3affa2a7b07648cd801e5b8199671911
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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