Potassium Carbonate → Tert-butyl 3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

HRID 1832145ノート

反応式

HRID 1832145 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+].C(N(C(C)C)CC)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 220489361,2,3,6-Tetrahydro-4-(3-nitrophenyl)pyridine

生成物 1

HCID 22049121Tert-butyl 3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate収率 86%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 2.80 g (14.0 mmol) of 1,2,3,6-tetrahydro-4-(3-nitrophenyl)pyridine, 3.60 g (15.0 mmol) of tert-butyl N-(3-bromopropyl)carbamate, 11.6 g (84.0 mmol) of K2CO3, 14.6 mL (84.0 mmol) of diisopropylethylamine and 0.78 g (2.00 mmol) of tetrabutylammonium iodide in 250 mL of 1,4-dioxane was heated at reflux temperature for 14 hours. The reaction mixture was filtered and the filtrate was dried (MgSO4), concentrated in vacuo and the residue was purified by column chromatography (silica, 9:1, dichloromethane:methanol+1% isopropyl amine) to afford 4.35 g (85.7% yield) of the desired product: 1H NMR (400 MHz, CDCl3) δ 8.24 (t, 1H, J=1.9 Hz), 8.09 (dd, 1H, J=1.9, 8.0 Hz), 7.70 (apparent d, 1H, J=8.0 Hz), 7.49 (t, 1H, J=8.0 Hz), 6.23 (m, 1H), 3.29–3.18 (m, 4H), 2.75 (t, 2H, J=5.6 Hz), 2.64–2.54 (m, 4H), 1.82–1.70 (m, 2H), 1.44 (s, 9H); ESMS m/e: 362.2 (M+H)+.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 14 hours
  3. filtrationThe reaction mixture was filtered
  4. dry with materialthe filtrate was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (silica, 9:1, dichloromethane:methanol+1% isopropyl amine)

出典と根拠

ORDレコード
ord-ed39f2076a4d4607bb23eb7bccedf765
出典データセット
uspto-grants-2006_06
特許番号
US07067534B1

反応ノート

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