2-(Dibenzylamino)-3-phenylpropanal → HCID 69017313, 화합물

HRID 1436491

반응식

HRID 1436491 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 69017313HCID 69017313, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d8ad7685d0a5440d903e8acc8f90740a
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618978B2

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