Acetone → HCID 19907424, compound

HRID 2371561Notes

Reaction equation

HRID 2371561 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][CH2:5][C:6](=[O:17])[CH2:7][CH2:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[BH4-].[Na+].CC(C)=O>CO>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:9]([OH:16])[CH2:8][CH2:7][CH:6]([OH:17])[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 19907374HCID 19907374, compound

Product 1

HCID 19907424HCID 19907424, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 95 mg of 1,10-bis(dimethylamino)-4,7-decanedione in 3 ml of methanol was added 36 mg of sodium borohydride with ice-cooling, and the mixture was stirred for an hour, and after adding 5 ml of acetone, concentrated under a reduced pressure. After adding chloroform, the mixture was again concentrated under reduced pressure. After adding 5 ml of chloroform, the mixture was filtered to remove insoluble matter, concentrated under a reduced pressure, and further dried under a reduced pressure to obtain 79 mg of the title compound comprising Syn/Anti (1:1) mixture as a yellow oil.

Workup

  1. temperaturecooling
  2. concentrationconcentrated under a reduced pressure
  3. additionAfter adding chloroform
  4. concentrationthe mixture was again concentrated under reduced pressure
  5. additionAfter adding 5 ml of chloroform
  6. filtrationthe mixture was filtered
  7. customto remove insoluble matter
  8. concentrationconcentrated under a reduced pressure
  9. customfurther dried under a reduced pressure

Sources & evidence

ORD record
ord-213bf53777cc4f2cb4072e19cd29f71f
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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