Methyl 7-(2,2-dimethylpropionylamino)-3-hydroxychroman-8-carboxylate → Methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate
Reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]2[C:9]([CH2:10][CH:11]([OH:20])[CH2:12][O:13]2)=[CH:8][CH:7]=1)=[O:4]>C(Cl)Cl>[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]2[C:9]([CH2:10][C:11](=[O:20])[CH2:12][O:13]2)=[CH:8][CH:7]=1)=[O:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
1,1,1-Tris-(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess Martin periodinane, 5.65 g) was added to a stirred solution of methyl 7-(2,2-dimethylpropionylamino)-3-hydroxychroman-8-carboxylate (Intermediate 11, 3.41 g) in DCM (50 mL) and the resultant mixture was stirred at room temperature for 5 hours. The resulting solution was washed with a 10% solution of sodium thiosulphate in saturated sodium bicarbonate solution, dried (Na2SO4) and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-30% to give methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate (2.26 g) as an off-white solid.
Workup
- washThe resulting solution was washed with a 10% solution of sodium thiosulphate in saturated sodium bicarbonate solution
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by chromatography on silica
- washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-30%
Sources & evidence
- ORD record
- ord-ef085b028b094e23bdd7f1fd530f23bf
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359369B2
Reaction notes
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