4-Fluorophenol → HCID 59909620, 화합물

HRID 1790425노트

반응식

HRID 1790425 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:28]([N:30]1[CH2:35][CH2:34][C@H:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37]2)[C@H:32]([CH2:45]O)[CH2:31]1)[CH3:29].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH2:28]([N:30]1[CH2:35][CH2:34][C@H:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37]2)[C@H:32]([CH2:45][O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:31]1)[CH3:29]

참가 물질

7

반응물 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59909613HCID 59909613, 화합물

생성물 1

HCID 59909620HCID 59909620, 화합물수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Under a nitrogen gas stream, 4-fluorophenol (168 mg) and triphenyiphosphine (420 mg) were added to a solution of cis-1-(1-ethyl-3-hydroxymethylpiperidin-4-yl)indoline (300 mg) in tetrahydrofuran (4 ml). After cooling the resultant mixture to −10° C., diethyl azodicarboxylate (278 mg) was gradually added dropwise thereinto. Then the resultant mixture was gradually warmed to room temperature and stirred at the same temperature overnight. After adding water (40 ml), the reaction mixture was extracted with ether (40 ml) for three times. The organic phase was washed successively with a saturated aqueous solution (40 ml) of sodium bicarbonate and a 1 N aqueous solution (40 ml) of sodium hydroxide, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia Chemical Ltd. NH-DM2035, hexane/ethyl acetate system) to give the title compound (100 mg) as a colorless oil (yield: 25%).

후처리

  1. extractionthe reaction mixture was extracted with ether (40 ml) for three times
  2. washThe organic phase was washed successively with a saturated aqueous solution (40 ml) of sodium bicarbonate
  3. dry with materiala 1 N aqueous solution (40 ml) of sodium hydroxide, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Fuji Silysia Chemical Ltd. NH-DM2035, hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-7f1244c632724b3dab3c580dc4dc560a
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071201B2

반응 노트

불러오는 중…