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

HRID 362544
ノート
印刷プレビュー

反応式

HRID 362544 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4ac5dc9cb654804b86208e3328ee031
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05869488

反応ノート

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