Diisopropylethylamine → Rac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-one

HRID 629318

Reaction equation

HRID 629318 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12]Br)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.Cl.[NH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:6]2[C:5]([CH2:12][N:15]([C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[OH:22])[C:7]2=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Product 1

HCID 118468159Rac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-oneYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 5-bromo-2-(bromomethyl)benzoate (0.50 g) in DMF (5.00 mL) were added trans-2-aminocyclohexanol hydrochloride (0.37 g) and N-ethyldiisopropylamine (1.42 mL), and the mixture was stirred at 80° C. for 3 hr. To the reaction mixture was added 5% aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.22 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23ffd78d87f04cde95c5344f099a46a1
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Linked notes

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