Triethylamine → (S)-2-(4-fluoro-benzylamino)-propionic acid methyl ester

HRID 11605

Reaction equation

HRID 11605 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([NH2:7])[CH3:6].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([NH:7][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([F:9])=[CH:11][CH:12]=1)[CH3:6]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 2733257Alanine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43230250(S)-2-(4-fluoro-benzylamino)-propionic acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (S)-2-amino-propionic acid methyl ester hydrochloride (25 g, 179 mmol) and 4-fluorobenzaldehyde (23 mL, 215 mmol) in 1,2-dichloroethane (200 mL) was added triethylamine (25 mL, 179 mmol). The resulting mixture was stirred for two hours at ambient temperature followed by addition of sodium triacetoxyborohydride (57 g, 268 mmol) in four portions. The resulting mixture was stirred overnight at ambient temperature. The reaction was neutralized with dilute aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (34.4 g).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06705e7a1e0948f294c7e03ad98290a8
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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