4-Methylbenzaldehyde → HCID 13316494, compound

HRID 485565Notes

Reaction equation

HRID 485565 reaction equation
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[BH4-].[Na+]>C(O)C>[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 447213phenylalaninol, (S)-HCID 4311764Sodium borohydride

Product 1

HCID 13316494HCID 13316494, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of L-phenylalaninol (6.0 g) and 4-methylbenzaldehyde (5.3 g) in ethanol (40 ml) was stirred for 30 minutes at room temperature. Sodium borohydride (2.0 g) was added in small portions with stirring and ice-cooling, and then the mixture was stirred for 1.5 hours at room temperature. After removal of the ethanol by evaporation, the residue was acidified with dilute hydrochloric acid and then made alkaline with aqueous sodium hydroxide. The resulting mixture was extracted with chloroform. The extract was dried over sodium sulfate and the solvent was evaporated. The residue was recrystallized from ethanol to give N-(4-methylbenzyl)-L-phenylalaninol (8.9 g), mp 125°-127° C., [α]D -6.7°.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 1.5 hours at room temperature
  3. customAfter removal of the ethanol
  4. customby evaporation
  5. extractionThe resulting mixture was extracted with chloroform
  6. dry with materialThe extract was dried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7eeb0dff65074e2cbac4f248d20299b6
Source dataset
uspto-grants-1985_08
Patent number
US04536601

Reaction notes

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