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

HRID 1348638

反応式

HRID 1348638 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c0e1b14399da4007b17d1580dce6c4c8
出典データセット
uspto-grants-2007_05
特許番号
US07211573B2

関連ノート

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