Benzaldehyde → HCID 29949005, compound

HRID 1951914Notes

Reaction equation

HRID 1951914 reaction equation
C(N(CC)CC)C.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[C:17]([O:21][CH2:22][C@@H:23]([C:25]([O:27][CH3:28])=[O:26])[NH2:24])([CH3:20])([CH3:19])[CH3:18].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:8]([NH:24][C@H:23]([C:25]([O:27][CH3:28])=[O:26])[CH2:22][O:21][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 16218549Methyl O-tert-butyl-L-serinate--hydrogen chloride (1/1)

Product 1

HCID 29949005HCID 29949005, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (9.5 ml, 68.0 mmol) and benzaldehyde (6.37 ml, 63.0 mmol) were added to a methanol (300 ml) solution of methyl O-tert-butyl-L-serinate hydrochloride (12.0 g, 57.0 mmol) and the resulting mixture was stirred at room temperature for 6 hours. Sodium borohydride (3.23 g, 86.0 mmol) was gradually added under ice cooling and then the resulting mixture was stirred at room temperature for 2 hours. An aqueous solution of saturated ammonium chloride (100 ml) was added to the reaction mixture. After concentration under reduced pressure, the residue was diluted with ethyl acetate and the precipitated insoluble matter was removed by filtration. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.3 g, 100%) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. concentrationAfter concentration under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. customthe precipitated insoluble matter was removed by filtration
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b904098c6ef343729f52abcc273eca0e
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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