N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide → N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

HRID 567070Notes

Reaction equation

HRID 567070 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][CH2:27][O:28][CH3:29])[S:22]([CH3:25])(=[O:24])=[O:23])C1C=CC=CC=1>C1COCC1.CO.[Pd].[C]>[CH3:19][C:14]1([CH3:20])[CH2:13][CH:12]([N:21]([CH2:26][CH2:27][O:28][CH3:29])[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 21264516N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

Product 1

HCID 17786848N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6 g of N-[6-benzyloxy-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide were dissolved in 100 ml of THF/methanol (1:1) and hydrogenated in a shaking duck using Pd/carbon. The crude product was crystallized using diisopropyl ether, 4.6 g, m.p. 115-117° C.

Workup

  1. customThe crude product was crystallized

Sources & evidence

ORD record
ord-17c2e7d5216c45949deae76f77c9f519
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

Loading…