Formaldehyde → HCID 22218302, compound

HRID 1795593Notes

Reaction equation

HRID 1795593 reaction equation
[CH3:1][C:2]1[C:3]([NH:15][C:16]2[CH:26]=[CH:25][C:19](C(OCC)=O)=[CH:18][CH:17]=2)=[CH:4][C:5]2[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]([CH3:12])[C:10]=2[CH:11]=1.[CH2:27]1COCC1.C=O.[BH3-]C#N.[Na+].[C:38]([O:41][CH2:42][CH3:43])(=[O:40])C>O.C(O)(=O)C>[CH3:27][C:18]1[CH:19]=[CH:25][C:26]([C:38]([O:41][CH2:42][CH3:43])=[O:40])=[C:16]([NH:15][C:3]2[C:2]([CH3:1])=[CH:11][C:10]3[C:9]([CH3:12])=[CH:8][CH2:7][C:6]([CH3:13])([CH3:14])[C:5]=3[CH:4]=2)[CH:17]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 22218329HCID 22218329, compound2×

Product 1

HCID 22218302HCID 22218302, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Following the previously described General Procedure D to a solution of ethyl 4-(3,5,8,8-tetramethyl-7,8-dihydronaphthalen-2-ylamino)benzoate (Compound 39, 0.10 g, 0.27 mmol) and 6 mL of THF was added an aqueous solution of formaldehyde 37% (0.20 mL, 2.7 mmol), followed by NaBH3CN (0.05 g, 0.82 mmol) and glacial acetic acid (5 mL). The resulting reaction mixture was stirred at room temperature for 24 h, then treated with water and ethyl acetate. The layers were separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with NaHCO3 1 N, brine, and dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by flash column (hexane:ethyl acetate=4:1) to give 0.050 g (50%) of the title compound as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with NaHCO3 1 N, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue was purified by flash column (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b68b5b8864ff4b44845631fdf647753c
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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