1,1-Dimethylhydrazine → HCID 21275436, compound

HRID 1381946Notes

Reaction equation

HRID 1381946 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:20][C:21]([OH:23])=O)([C:17](O)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:39][N:40]([CH3:42])[NH2:41]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([C:17](=[O:18])[N:41]([N:40]([CH3:42])[CH3:39])[C:21](=[O:23])[CH2:20]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 10868DicyclohexylcarbodiimideHCID 14371890HCID 14371890, compound

Product 1

HCID 21275436HCID 21275436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1-benzyloxycarbonyl-4-carboxy-piperidin-4-yl)acetic acid (1.28 g) in dimethylformamide (10 ml) was added dicyclohexylcarbodiimide (0.82 g), and this was followed by 30 minutes of stirring at room temperature. 1,1-Dimethylhydrazine (0.62 ml) was then added, and this was also followed by 30 minutes of stirring at room temperature. The solvent was then evaporated under reduced pressure. To the resulting residual oily compound were added acetic anhydride (10 ml) and then anhydrous sodium acetate (0.33 g), and this was followed by stirring at 100° C. for 30 minutes. The solvents were then evaporated under reduced pressure. The resulting residual substance was dissolved in ethyl acetate (50 ml), and it was washed with a saturated aqueous solution of sodium hydrogen-carbonate and then with water. The organic layer was then dried with anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure to yield an oily substance. This oily substance was separated by silica gel column chromatography (eluent; methanol-dichloromethane=1:19 (v/v)), and the solvent for the solution containing the desired product was evaporated to obtain 0.71 g of a colorless oil.

Workup

  1. waitthis was also followed by 30 minutes
  2. stirringof stirring at room temperature
  3. customThe solvent was then evaporated under reduced pressure
  4. additionTo the resulting residual oily compound were added acetic anhydride (10 ml)
  5. stirringby stirring at 100° C. for 30 minutes
  6. customThe solvents were then evaporated under reduced pressure
  7. dissolutionThe resulting residual substance was dissolved in ethyl acetate (50 ml)
  8. washit was washed with a saturated aqueous solution of sodium hydrogen-carbonate
  9. dry with materialThe organic layer was then dried with anhydrous magnesium sulfate
  10. customthe solvent was then evaporated under reduced pressure
  11. customto yield an oily substance
  12. customThis oily substance was separated by silica gel column chromatography (eluent; methanol-dichloromethane=1:19 (v/v))
  13. additionthe solvent for the solution containing the desired product
  14. customwas evaporated

Sources & evidence

ORD record
ord-967a8c3ee898405e8ab20a06e6693acf
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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