Acetic Acid → HCID 14181063, compound

HRID 1494572Notes

Reaction equation

HRID 1494572 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][C:14](=O)[CH2:13][CH2:12]2.[NH2:18][CH2:19][CH2:20][N:21](CC)[C:22](=[O:24])[O-:23].[C:27](O)(=O)[CH3:28]>>[CH2:27]([O:23][C:22]([NH:21][CH2:20][CH2:19][NH:18][CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([O:6][CH3:5])[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)=[O:24])[CH3:28]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 41360218-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydrideHCID 21616286N-(2-aminoethyl)ethylcarbamate

Product 1

HCID 14181063HCID 14181063, compoundYield 46.2%

Procedure

10.0 g (159 mmol) of sodium cyanoborohydride were added to the solution of 7.00 g (40 mmol) of 8-methoxy-2-tetralone, 8.00 g (61 mmol) of N-(2-aminoethyl)ethylcarbamate and 9.60 g (160 mmol) of glacial acetic acid at 0° C. After 15 hours at room temperature, the mixture was concentrated, taken up in tert.-butyl methyl ether, and treated with water. The pH of the aqueous phase was adjusted to 10 using sodium hydroxide solution. The mixture was stirred vigorously for 30 minutes. The organic phase was separated off, and the aqueous phase was extracted thoroughly with the last-mentioned solvent. Drying the organic phase and concentrating supplied an oil, which was purified by chromatography on silica gel (toluene/ ethanol gradients with addition of 0.3% triethylamine). 5.40 g (46%) of the pure title compound were obtained as a brownish oil.

Workup

  1. concentrationthe mixture was concentrated
  2. additiontreated with water
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted thoroughly with the last-mentioned solvent
  5. customDrying the organic phase
  6. concentrationconcentrating
  7. customwas purified by chromatography on silica gel (toluene/ ethanol gradients with addition of 0.3% triethylamine)

Sources & evidence

ORD record
ord-5aee70d537194a1fa710d09822451a00
Source dataset
uspto-grants-1991_06
Patent number
US05026857

Reaction notes

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