Potassium Hydroxide → HCID 66798876, compound

HRID 1193293Notes

Reaction equation

HRID 1193293 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([C@H:14]1[C:23]3[C:18](=[C:19]([F:28])[CH:20]=[C:21]([C:24]([O:26]C)=[O:25])[CH:22]=3)[O:17][CH2:16][CH2:15]1)[CH2:9]2>C(O)C.O>[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([C@H:14]1[C:23]3[C:18](=[C:19]([F:28])[CH:20]=[C:21]([C:24]([OH:26])=[O:25])[CH:22]=3)[O:17][CH2:16][CH2:15]1)[CH2:9]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 66798701HCID 66798701, compound

Product 1

HCID 66798876HCID 66798876, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (1 mol/l aq) (2 eq) was added to a suspension of (R)-methyl 4-(7-chloro-1-oxoisoindolin-2-yl)-8-fluorchromane-6-carboxylate (D-05) (0.8 mmol, 1 eq) in a mixture of ethanol (4.6 ml) and water (1.6 ml). The reaction mixture was stirred overnight at RT. Ethanol was removed in vacuo and the residue was taken up in diethyl ether and water. The phases were separated and the aqueous phase was adjusted to pH 3 with 1N HCl. The aqueous phase was extracted with ethyl acetate (3×) and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate:cyclohexane 1:1). Yield: 62% B. Amine Structural Units Overview: Amine Structural Units

Workup

  1. customEthanol was removed in vacuo
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, ethyl acetate:cyclohexane 1:1)

Sources & evidence

ORD record
ord-0ce0783049ef4bfca50ab99e40cd0b91
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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