Formaldehyde → HCID 86596682, compound

HRID 1445346Notes

Reaction equation

HRID 1445346 reaction equation
[C:1]([O:5][C:6]([N:8](C)[CH:9]1CCN(C(OCC2C=CC=CC=2)=O)C(CO)C1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:28]1[CH2:33][CH:32]=[CH:31][CH2:30][CH:29]=1.C=[O:35].[BH3-][C:37]#[N:38].[Na+]>CCO.CO.[Pd].CC(O)=O>[OH:35][CH2:28][CH:33]1[CH2:32][CH:31]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:30][CH2:29][N:38]1[CH3:37]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 123431,4-CyclohexadieneHCID 5003444Sodium cyanoborohydrideHCID 59854979HCID 59854979, compound

Product 1

HCID 86596682HCID 86596682, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 1.08 g (2.9 mmol) of 2-2 in 30 mL of EtOH was added 7 mL (74 mmol) of 1,4-cyclohexadiene and a catalytic amount of 10% Pd on carbon. After stirring overnight, the reaction was filtered through Celite, concentrated by rotary evaporation, and dissolved in 25 mL of MeOH. To this was added 2 mL of AcOH, and 700 μL (8.6 mmol) of 37% aqueous formaldehyde. After stirring overnight, 540 mg (8.6 mmol) of NaCNBH3 in 5 mL of MeOH was added and the reaction was stirred for 1 h more. The solvents were removed by rotary evaporation, the residue was partitioned between EtOAc and aqueous NaHCO3, the organic phase was washed with brine, dried over Na2SO4, and concentrated. The residue was taken up in CH2Cl2, filtered and concentrated to provide 2-3 as a colorless oil. Data for 2-3: LRMS (ES) calc'd M+H for C13H26N2O3: 259. Found: 259.

Workup

  1. filtrationthe reaction was filtered through Celite
  2. concentrationconcentrated by rotary evaporation
  3. dissolutiondissolved in 25 mL of MeOH
  4. stirringAfter stirring overnight
  5. stirringthe reaction was stirred for 1 h more
  6. customThe solvents were removed by rotary evaporation
  7. customthe residue was partitioned between EtOAc and aqueous NaHCO3
  8. washthe organic phase was washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-bb542fa2634f4d84903e884d0c99ee4a
Source dataset
uspto-grants-2010_02
Patent number
US07666862B2

Reaction notes

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