Acetone → 2-Dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester

HRID 1348638

Reaction equation

HRID 1348638 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH3:30][C:31]([CH3:33])=[O:32].[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:31]([OH:32])([CH3:33])[CH3:30])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 3553452Ethyl 2-(dibenzylamino)acetate

Product 1

HCID 148244862-Dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl esterYield 52.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.3 g (40.0 mmol) dibenzylamino-acetic acid ethyl ester in 107 ml tetrahydrofuran and 107 ml toluene was stirred at −70° C. with 22 ml (44 mmol) lithium diisopropylamide (2M in heptane) for 30 minutes. 3.40 ml (46 mmol) acetone were added and stirring was continued overnight. The mixture was allowed to warm to room temprature, aqueous ammonium chloride solution was added. Extraction with diethylether and chromatography on silicagel with diethylether/heptane 1/2 yielded 7.16 g (52%) 2-dibenzylamino-3-hydroxy-3-methyl-butyric acid ethyl ester, MS m/e (%): 342.3 (M+H+, 100).

Workup

  1. additionwas added
  2. extractionExtraction with diethylether and chromatography on silicagel with diethylether/heptane 1/2

Sources & evidence

ORD record
ord-c0e1b14399da4007b17d1580dce6c4c8
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Linked notes

Loading…