4-Fluorophenol → HCID 59909620, compound

HRID 1790425Notes

Reaction equation

HRID 1790425 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 59909620HCID 59909620, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-7f1244c632724b3dab3c580dc4dc560a
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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