N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide → N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide

HRID 567059Notes

Reaction equation

HRID 567059 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([CH2:26][CH3:27])[S:22]([CH3:25])(=[O:24])=[O:23])C1C=CC=CC=1>C1COCC1.CO.[Pd].[C]>[CH3:20][C:14]1([CH3:19])[CH2:13][CH:12]([N:21]([CH2:26][CH3:27])[S:22]([CH3:25])(=[O:24])=[O:23])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[O:15]1

Participants

4

Reactant 1

HCID 21264511N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide

Product 1

HCID 17786837N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

12 g of N-[6-benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide were dissolved in 250 ml of THF/methanol (1:1) and hydrogenated in a shaking duck using Pd/carbon. After absorption of hydrogen was complete, the catalyst was filtered off with suction, the filtrate was concentrated and the residue was crystallized using diisopropyl ether, 7.7 g, m.p. 169-170° C.

Workup

  1. customAfter absorption of hydrogen
  2. filtrationthe catalyst was filtered off with suction
  3. concentrationthe filtrate was concentrated
  4. customthe residue was crystallized

Sources & evidence

ORD record
ord-2a1be54814304987a3e4c44758b8391f
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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