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

HRID 1832145노트

반응식

HRID 1832145 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ed39f2076a4d4607bb23eb7bccedf765
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067534B1

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