Acetaldehyde → HCID 9947152, compound

HRID 1795582Notes

Reaction equation

HRID 1795582 reaction equation
[CH3:1][C:2]1[C:3]([NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O-:22])=[O:21])=[CH:18][CH:17]=2)=[CH:4][C:5]2[C:6]([CH3:14])=[CH:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH2:25]1COC[CH2:26]1.[CH:30](=O)C.[BH3-]C#N.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C>[CH2:14]([C:6]1[C:5]2[CH:4]=[C:3]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:25][CH3:26])=[O:21])=[CH:23][CH:24]=3)[C:2]([CH3:1])=[CH:11][C:10]=2[C:9]([CH3:12])([CH3:13])[CH2:8][CH:7]=1)[CH3:30]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 22218201HCID 22218201, compound2×

Product 1

HCID 9947152HCID 9947152, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

General Procedure D To a solution of 4-[(3,5,5,8-Tetramethyl-5,6-dihydronaphthalen-2-yl)amino]benzoate (Compound 15, 0.20 g, 0.58 mmol) and 5 mL of THF was added acetaldehyde (0.30 mL, 5.8 mmol), followed by NaBH3CN (0.10 g, 1.74 mmol) and glacial acetic acid (2 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 0.19 g (88%) of the title compound as a light 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-6b1e579f68e94edb9f6923d309b065c4
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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