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Sodium cyanoborohydride → 6-(4-(4-Nitrophenethyl)-3-oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466117
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HRID 1466117 반응식
O=[C:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5][C:4]=2[CH2:3]1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][C:26]2=[O:31])=[CH:19][CH:18]=1)([O-:16])=[O:15].C([BH3-])#N.[Na+]>C(O)C.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH:2]3[CH2:11][CH2:10][C:9]4[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5][C:4]=4[CH2:3]3)[CH2:27][C:26]2=[O:31])=[CH:21][CH:22]=1)([O-:16])=[O:15]
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참가 물질

7

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileHCID 895248911-[2-(4-Nitrophenyl)ethyl]piperazin-2-one

생성물 1

HCID 715256856-(4-(4-Nitrophenethyl)-3-oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매
HCID 702Ethanol용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (24 mg, 0.14 mmol) and 1-[2-(4-nitrophenyl)ethyl]piperazin-2-one (20 mg, 0.070 mmol) was treated with titanium(IV) isopropoxide (0.10 ml, 0.35 mmol) for 30 minutes. Then the reaction was diluted with ethanol (5 mL), and sodium cyanoborohydride (44 mg, 0.70 mmol) was added. The reaction was stirred at RT overnight. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated to give the crude residue. The desired product was purified by reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 405 [M+1]+.

후처리

  1. additionwas added
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca3a5800606842b7a85fa0f0b6009b19
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999990B2

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