(+/-)-trans-N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide → N-(3,6-dihydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

HRID 613444Notes

Reaction equation

HRID 613444 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])[C@@H:13]([OH:21])[C@@H:12]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])C1C=CC=CC=1.[H][H]>C1COCC1.CO.[Pd]>[OH:21][CH:13]1[CH:12]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[O:15][C:14]1([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 15860270(+/-)-trans-N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19593317N-(3,6-dihydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.0 g (2.6 mmol) of (±)-trans-N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide (Example 1) was hydrogenated in 100 ml of THF/methanol (1:1) in the presence of palladium/carbon until the uptake of hydrogen had ended. The catalyst was filtered off and the filtrate was concentrated, giving 0.7 g of N-(3,6-dihydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide; m.p. 204-206° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-223e9d1110014041abb6235b10f6f176
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

Loading…