Formaldehyde → HCID 45116063, compound

HRID 2371386Notes

Reaction equation

HRID 2371386 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1)=[O:4].[CH2:12]=O.[H][H]>C(O)(=O)C.O.[Pt]=O>[CH3:12][N:6]1[CH2:7][C@H:8]([OH:10])[CH2:9][C@H:5]1[C:3]([N:2]([CH3:11])[CH3:1])=[O:4]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 23535509HCID 23535509, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 45116063HCID 45116063, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of (2S,4R)-2-dimethylaminocarbonyl-4-hydroxypyrrolidine (2.0 g) in acetic acid (14.4 ml) and water (8 ml), 37% aqueous formaldehyde solution (1.27 g) and platinum oxide (38 mg) were added, and the mixture was hydrogenated at room temperature for 7 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent. The residue was dissolved in dichloromethane and dried over magnesium sulfate. Potassium carbonate (3.5 g) was added thereto, and the mixture was stirred for 1.5 hours, followed by filtration. Removal of the solvent gave (2S,4R)-1-methyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. additionPotassium carbonate (3.5 g) was added
  7. filtrationfollowed by filtration
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-97fde838fbe5403d95c4b7b6bae10429
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

Loading…