Formaldehyde → HCID 70453855, compound

HRID 2290924Notes

Reaction equation

HRID 2290924 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@@H:9]([CH2:10][NH:11][CH2:12]3)[C:8]=2[CH:7]=[CH:6][C:5]=1[O:17][CH3:18].[CH2:19]=O>[Pd].CO>[ClH:1].[CH3:2][O:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@@H:9]([CH2:10][N:11]([CH3:19])[CH2:12]3)[C:8]=2[CH:7]=[CH:6][C:5]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 70453900HCID 70453900, compound

Product 1

HCID 70453855HCID 70453855, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product of example 46, formalin (5 mL), NaOAc.3H2O (0.45 g), and MeOH (95 mL) in the presence of Pd/C catalyst (0.45 g, 5%, wet) was hydrogenated under 3 atmospheres H2 pressure. The resulting solution was filtered and evaporated to dryness. Water/1N KOH were added and the solution was extracted with ether. The combined extracts were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, evaporated, and converted to the HCl salt. The crude product was triturated with ether/MeOH, filtered, and dried to yield 0.70 g gray powder, (75%); mp 228°-30° C.; M+ 247.

Workup

  1. filtrationThe resulting solution was filtered
  2. customevaporated to dryness
  3. additionWater/1N KOH were added
  4. extractionthe solution was extracted with ether
  5. washThe combined extracts were washed with water, saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was triturated with ether/MeOH
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-6ca4253cdf7148629b4be1890fafa12a
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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