Triethylamine → tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

HRID 416775

反応式

HRID 416775 の反応式
N1C=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH3:8].[N:22]1C=CC=C(C(O)C)[CH:23]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(N1CCNCC1)(OC(C)(C)C)=O>CS(C)=O.CCOC(C)=O.CO.C(Cl)Cl>[N:22]1[CH:5]=[CH:4][CH:3]=[C:2]([CH:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH3:8])[CH:23]=1

参加物

9

反応物 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 101192alpha-Methyl-3-pyridinemethanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 60137623tert-Butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate2 回

生成物 1

HCID 66622025tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒HCID 21584119Ethylacetate methanol溶媒

実験手順

This was prepared using the same procedure as for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, but here using 1-(pyridin-3-yl)ethanol (J. Chem. Soc., Perkin Trans. 1, 2000, 4439-4444) (200 mg, 1.62 mmol), triethylamine (5.0 eq, 8.12 mmol, 1.13 mL), MsCl (2.0 eq, 3.25 mmol, 0.26 mL), CH2Cl2 (8 mL) at 0° C. for 30 minutes. A solution of ether-pentane (1:1, 20 mL) was added, the solid removed by filtration and the solvents removed in vacuo. The residue was then treated with N—BOC piperazine (4.0 eq, 6.50 mmol, 1.21 g) in DMSO (6 mL) at 60° C. for 18 h. Work up as described for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, followed by column chromatography (EtOAc-MeOH, 95:5) gave the product (186 mg, 39% for two steps) as a colourless oil; 1H-NMR (500 MHz, CDCl3) 1.36 (d, J=6.8 Hz, 3H, CH3), 1.42 (s, 9H, C(CH3)3), 2.29-2.45 (m, 4H, piperazine N(CH2)2), 3.38 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.45 (q, J=6.8 Hz, 1H, CH), 7.23 (dd, br, J=7.9, 4.7 Hz, 1H, pyridine H-5), 7.64 (dt, J=7.8, 1.9 Hz, 1H, pyridine H-4), 8.47 (dd, J=4.8, 1.8 Hz, 1H, pyridine H-6), 8.52 (d, br, J=1.9 Hz, 1H, pyridine H-2);

後処理

  1. customThis was prepared
  2. customat 0° C.
  3. customfor 30 minutes
  4. customthe solid removed by filtration
  5. customthe solvents removed in vacuo
  6. customgave the product (186 mg, 39% for two steps) as a colourless oil

出典と根拠

ORDレコード
ord-eb915e51ed0f4cb4b0239007b64ae9a0
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

関連ノート

読み込み中…