Triethylamine → tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetate

HRID 25681Notes

Reaction equation

HRID 25681 reaction equation
C(N(CC)CC)C.[CH:8]1[CH:13]=[CH:12][C:11]([C@H:14]([NH2:17])[CH2:15][OH:16])=[CH:10][CH:9]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[Cl-].[NH4+]>O1CCCC1>[OH:16][CH2:15][C@@H:14]([NH:17][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 1347972-Amino-2-phenylethan-1-ol

Product 1

HCID 59065869tert-butyl (S)-(2-hydroxy-1-phenyl-ethylamino)-acetateYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the literature procedure (Panek, J., J. Org. Chem., 1998, 63, 2382), triethylamine (6.2 ml, 44.5 mmole) was added to a solution of (S)-phenylglycinol (5 g, 36.45 mmole) in anhydrous tetrahydrofuran (150 ml) under argon at 0° C. After stirring for 15 min, tert-butyl bromoacetate (5.9 ml, 39.96 mmole) was added slowly to this cooled solution. The resulting mixture was warmed to room temperature, and stirred for 15 h. Saturated ammonium chloride aqueous solution was added, and the aqueous layer was extracted with diethyl ether (3 times). The combined extracts were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. The resulting solid was recrystallized from a diethyl ether/n-hexane mixture to give tert-butyl (S)-(2-Hydroxy-1-phenyl-ethylamino)-acetate as a white solid (3 g, 33%).

Workup

  1. stirringstirred for 15 h
  2. extractionthe aqueous layer was extracted with diethyl ether (3 times)
  3. washThe combined extracts were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo
  7. customThe resulting solid was recrystallized from a diethyl ether/n-hexane mixture

Sources & evidence

ORD record
ord-4155ccae976a4f078fbd239bf2b9a877
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

Loading…