Triethylamine → HCID 54566785, compound

HRID 480178Notes

Reaction equation

HRID 480178 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[BH3-])(=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 11182647Methyl D-alaninate hydrochlorideHCID 23670382Sodiumacetoxyborohydride

Product 1

HCID 54566785HCID 54566785, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (R)-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 acetoxyborohydride (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 (2×). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (34.4 g, 91% yield).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc0b56c2a3844b9da710ba81663d0cda
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

Loading…