Water → (R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 2389107노트

반응식

HRID 2389107 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][B-](F)(F)F)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[K+].ClCCl.FC(F)(F)S(O[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C@:36]3([CH3:42])[CH2:40][O:39][C:38](=[O:41])[NH:37]3)[CH:32]=2)[CH:27]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1.O>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([C@:36]2([CH3:42])[CH2:40][O:39][C:38](=[O:41])[NH:37]2)[CH:30]=[CH:29]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 6

HCID 962WaterHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 86642894(R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonateHCID 87390053Potassium 4-tert-butylcyclohexylmethyltrifluoroborate

생성물 1

HCID 67415438(R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one수율 12.8%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A solution of potassium 4-tert-butylcyclohexylmethyltrifluoroborate (100 mg, 0.0004 mol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (31.4 mg, 0.0000384 mol), (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate (144 mg, 0.000384 mol) and cesium carbonate (0.376 g, 0.00115 mol) in 1,4-dioxane (4.6 mL, 0.059 mol) and water (0.5 mL, 0.03 mol) was heated at reflux under a nitrogen atmosphere. The reaction mixture was stirred at 100° C. overnight, then cooled to room temperature, and diluted with EtOAc, filtrate, followed by extraction of ether. The organic layers were combined and dried over MgSO4, and filtered. The concentrated residue was chromatographed with silica gel under 0-100% EtOAc/hexane to give (R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one as a solid (18.6 mg, 12.8%). 1H NMR (400 MHz, CHLOROFORM-d) δ=7.84 (d, J=8.7 Hz, 1 H), 7.79 (br. s., 1 H), 7.77 (d, J=8.5 Hz, 1 H), 7.60 (s, 1 H), 7.45 (dd, J=1.9, 8.6 Hz, 1 H), 7.38 (d, J=8.4 Hz, 1 H), 5.83 (br. s., 1 H), 4.46-4.39 (m, 2 H), 2.82 (d, J=7.9 Hz, 2 H), 2.09 (m., 1 H), 1.87 (s, 3 H), 1.68-1.40 (m, 5 H), 1.39-1.24 (m, 2 H), 1.08-0.96 (m, 1 H), 0.91 (s, 9 H).

후처리

  1. temperatureat reflux under a nitrogen atmosphere
  2. temperaturecooled to room temperature
  3. extractionfollowed by extraction of ether
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe concentrated residue was chromatographed with silica gel under 0-100% EtOAc/hexane

출처 및 근거

ORD 기록
ord-6b7ac2ecbf6f445f93b7d583141d1317
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269043B2

반응 노트

불러오는 중…