2-(Dibenzylamino)-3-phenylpropanal → HCID 69017313、化合物

HRID 1436491

反応式

HRID 1436491 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13](=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:29]([N:36]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:37]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:38]=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH2:47]([N:36]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@@H:37]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:38]([CH:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][CH2:15][N:14]([CH3:17])[C:13]1=[O:18])[OH:39])[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

参加物

5

反応物 3

HCID 5638962-(Dibenzylamino)-3-phenylpropanalHCID 2733832Lithium HexamethyldisilazideHCID 586385404-Cbz-1-methyl-2-piperazinone

生成物 1

HCID 69017313HCID 69017313、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Treat a solution of 4-benzyloxycarbonyl-1-methylpiperazin-2-one (1.4 g, 5.7 mmol) in THF (4 mL) cooled at −78° C. with lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 5.7 mL, 5.7 mmol) dropwise and stir 30 min. Add 2-(dibenzylamino)-3-phenylpropanal (1 g, 3.1 mmol) in THF (2 mL) and stir at −78° C. for 45 min. Quench with saturated aqueous ammonium chloride solution. Separate organic layer and wash with water, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate) to provide the title compound as a mixture of four diastereoisomers which are separated by HPLC (normal phase, eluting with 85:15 hexanes:isopropanol) (828 mg, 45% total yield).

後処理

  1. customQuench with saturated aqueous ammonium chloride solution
  2. washSeparate organic layer and wash with water, saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-d8ad7685d0a5440d903e8acc8f90740a
出典データセット
uspto-grants-2009_11
特許番号
US07618978B2

関連ノート

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