Formaldehyde → HCID 54378998, compound

HRID 428455Notes

Reaction equation

HRID 428455 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:8]2([CH2:11][NH:10][CH2:9]2)[CH2:7][N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5]1.C=O.[C:21]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(O)C>[CH2:12]([N:6]1[CH2:5][C:4](=[N:3][O:2][CH3:1])[C:8]2([CH2:11][N:10]([CH3:21])[CH2:9]2)[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 53707904HCID 53707904, compound

Product 1

HCID 54378998HCID 54378998, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

550 mg of 6-benzyl-2,6-diazaspiro[3,4]octane-8-one-O-methyloxime was added to 10 ml of ethanol and thereto 0.4 ml of acetic acid and 176 mg of paraformaldehyde were added and the resulting mixture was stirred for 30 minutes at room temperature and thereto 370 mg of sodium cyanoborohydride was added. The resulting mixture was stirred for 16 hours at room temperature, neutralized with aqueous solution of potassium carbonate and distilled under the reduced pressure and the obtained residue was added into 50 ml of dichloromethane, washed with 50 ml of water, dried with magnesium sulfate, filtered and concentrated under the reduced pressure. The residue was purified by silicagel column chromatography(methanol:normal hexane:dichloromethane=1:10:8) to give 350 mg of the titled compound(yield: 60.1%).

Workup

  1. stirringThe resulting mixture was stirred for 16 hours at room temperature
  2. distillationdistilled under the reduced pressure
  3. additionthe obtained residue was added into 50 ml of dichloromethane
  4. washwashed with 50 ml of water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under the reduced pressure
  8. customThe residue was purified by silicagel column chromatography(methanol:normal hexane:dichloromethane=1:10:8)

Sources & evidence

ORD record
ord-b26fe753a6bc4ef3979db7fab4d5935b
Source dataset
uspto-grants-2001_11
Patent number
US06313299B1

Reaction notes

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