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8-Benzyl-8-azabicyclo(3.2.1)octan-3-one → Ammonia

HRID 362544
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인쇄 미리보기

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HRID 362544 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][N:13]([C:15](=[O:24])[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=3)[CH2:12][CH2:11][N:10]2[C:25](=[O:42])[CH2:26][NH:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:30][CH:29]2[CH3:41])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:44]C(N1CCN(C(=O)C2C=C(C)C=C(C)C=2)CC1C1C=CC(Cl)=C(Cl)C=1)=O.C(N1C2CCC1CC(=O)C2)C1C=CC=CC=1.[BH3-]C#N.[Na+]>O>[NH3:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][N:13]([C:15](=[O:24])[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=3)[CH2:12][CH2:11][N:10]2[C:25](=[O:42])[CH2:26][NH:27][CH:28]2[CH2:44][CH:30]3[N:31]([CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:32]([CH2:41][CH2:29]3)[CH2:33]2)[CH:5]=[CH:6][C:7]=1[Cl:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 5003444Sodium cyanoborohydrideHCID 10277726(+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazineHCID 15887547(+,-)-2-(3,4-Dichlorophenyl)-4-[3,5-dimethylbenzoyl]-1-[[[3-methyl-1-(phenylmethyl)-4-piperidinyl]amino]acetyl]piperazine

생성물 2

HCID 222Ammonia
HCID 44214921
2-(3,4-Dichlorophenyl)-4-(3,5-dimethylbenzoyl)-1-[[[8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]amino]acetyl]piperazine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

By an analogous method to that described in Example 16, the product from Example 16, compound 3 (185 mg, 0.44 mmol) was combined with 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (97 mg, 0.45 mmol) and Ti(O-i Pr)4 (105 mL, 0.50 mmol) and left stirring for 1 h. To the thick reaction mixture was added NaBH3CN (59.5 mg, 0.95 mmol) and the mixture was stirred overnight. To the reaction mixture was added H2O (1 mL) and it was filtered. The filtrate was washed with EtOH, concentrated and purified by silica gel chromatography, eluting with 30:1:0.1 to 15:1:0.1 CH2Cl2 --MeOH--NH3 aq. to give the title product as a white foam. HRMS (FAB, M+H+); m/e calc'd [C35H41Cl2N4O2 ]+ : 619.2607, found 619.2594.

후처리

  1. waitleft
  2. stirringthe mixture was stirred overnight
  3. filtrationwas filtered
  4. washThe filtrate was washed with EtOH
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography
  7. washeluting with 30:1:0.1 to 15:1:0.1 CH2Cl2

출처 및 근거

ORD 기록
ord-f4ac5dc9cb654804b86208e3328ee031
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05869488

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