HCID 66741339, compound → ethyl 1-benzyl-1-hydroxy-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 587874Notes

Reaction equation

HRID 587874 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])[C:9]2=[O:12])=[CH:5][CH:4]=1>O1CCCC1>[CH2:7]([C:9]1([OH:12])[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH:8]1[NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])[C:6]1[CH:10]=[CH:11][CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 1

HCID 66741339HCID 66741339, compound

Product 1

HCID 66741247ethyl 1-benzyl-1-hydroxy-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To ice cold 2M benzylmagnesium chloride in tetrahydrofuran (6.14 ml, 12.28 mmol) was added dropwise a solution of ethyl 6-methoxy-1-oxo-2,3-dihydro-1H-inden-2-ylcarbamate (1.02 g. 4.09 mmol) in tetrahydrofuran (30 ml) and stirred over night, while the reaction mixture was allowed to warm up to room temperature. The reaction mixture was quenched with sat. ammonium chloride and the organic layer was evaporated. The residue was extracted twice with dichloromethane and the combined organic layers were washed subsequently with sodium bicarbonate and brine, dried, filtered and evaporated to obtain a dark gooey oil, that was purified by flash silica gel chromatography on 12 g SiO2— cartridge using 30% ethyl acetate in cyclohexane to afford the desired ethyl 1-benzyl-1-hydroxy-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate as a brown grease. m=1.07 g (77%)

Workup

  1. customThe reaction mixture was quenched with sat. ammonium chloride
  2. customthe organic layer was evaporated
  3. extractionThe residue was extracted twice with dichloromethane
  4. washthe combined organic layers were washed subsequently with sodium bicarbonate and brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a dark gooey oil, that
  9. customwas purified by flash silica gel chromatography on 12 g SiO2— cartridge

Sources & evidence

ORD record
ord-44567daa0b6544e1b6c85a13613dc4b4
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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