2-Methoxy-1-naphthaldehyde → HCID 69364316, compound

HRID 1281091Notes

Reaction equation

HRID 1281091 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=O.[C:15]([O:19][C:20](=[O:24])[CH2:21][CH2:22][NH2:23])([CH3:18])([CH3:17])[CH3:16].[BH4-].[Na+]>S([O-])([O-])(=O)=O.[Mg+2].ClCCl>[C:15]([O:19][C:20](=[O:24])[CH2:21][CH2:22][NH:23][CH2:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 793522-Methoxy-1-naphthaldehydeHCID 4192171tert-Butyl 3-aminopropanoateHCID 4311764Sodium borohydride

Product 1

HCID 69364316HCID 69364316, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 18426670HCID 18426670, compoundSolvent

Procedure

To a solution of 0.559 g (3 mmol) 2-methoxynaphthaldehyde and 0.436 g (3 mmol) 3-aminopropionic acid tert-butyl ester in 6 ml of dichloromethane magnesium sulphate was added and the mixture was shaken for 18 h at room temperature. Magnesium sulphate was separated from the reaction mixture and washed two times with dichloromethane. After evaporating the combined organic layers the residue was re-dissolved in methanol. To the stirred and cooled (0° C.) solution 227 mg (6 mmol) sodium borohydride was added in small portions. Stirring was continued for 1 h at 0° C. Methanol was evaporated, water (50 ml) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, petrolether/ether=1:1) to yield 297 mg (31%) of the title compound.

Workup

  1. customMagnesium sulphate was separated from the reaction mixture
  2. washwashed two times with dichloromethane
  3. customAfter evaporating the combined organic layers the residue
  4. dissolutionwas re-dissolved in methanol
  5. stirringTo the stirred
  6. additionwas added in small portions
  7. stirringStirring
  8. waitwas continued for 1 h at 0° C
  9. customMethanol was evaporated
  10. additionwater (50 ml) was added
  11. extractionthe mixture was extracted three times with ethyl acetate
  12. dry with materialThe combined organic layers were dried (MgSO4)
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by column chromatography (SiO2, petrolether/ether=1:1)

Sources & evidence

ORD record
ord-83d17a7041a2462ba31ad8009f386c2f
Source dataset
uspto-grants-2002_09
Patent number
US06452001B2

Reaction notes

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