Toluene → (3R,9S)-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-4-(prop-1-en-2-yl)-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

HRID 573787노트

반응식

HRID 573787 반응식
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13](Cl)[C:12]3[C@@H:22]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)[O:23][C:24]4([CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:40]([B-](F)(F)F)([CH3:42])=[CH2:41].[K+].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([C:40]([CH3:42])=[CH2:41])[C:12]3[C@@H:22]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)[O:23][C:24]4([CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborateHCID 86662528(3R,9S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

생성물 1

HCID 66762113(3R,9S)-9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-4-(prop-1-en-2-yl)-3-(4-(trifluoromethyl)phenyl)-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
100 °C

실험 절차

500 mg (3R,9S)-9-(tert-butyldimethylsilyloxy)-4-chloro-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran] and 254 mg potassium isopropenyltrifluoroborate are dissolved in 3 ml tetrahydrofurane, 0.5 ml toluene and 3 ml of a 2 M solution of caesium carbonate in water. The mixture is purged for 15 minutes with argon. Then 42 mg 1,1′-bis-(diphenylphosphino)-ferrocene-dichloro-palladium-(II) complex with dichloromethane are added and the mixture is stirred for 72 hours at 100° C. The mixture is partitioned between water and dichloromethane. The aqueous phase is twice extracted with dichloromethane. The combined organic phases are dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 90:10).

후처리

  1. customThe mixture is purged for 15 minutes with argon
  2. additionThen 42 mg 1,1′-bis-(diphenylphosphino)-ferrocene-dichloro-palladium-(II) complex with dichloromethane are added
  3. customThe mixture is partitioned between water and dichloromethane
  4. extractionThe aqueous phase is twice extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customthe solvents are evaporated in vacuo
  7. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 90:10)

출처 및 근거

ORD 기록
ord-aaf0ad7baf6945f282604a75c366ab49
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029544B2

반응 노트

불러오는 중…