Sodium Bicarbonate → 4-(3-Bromo-4,5-dimethoxyphenyl)-7-dimethylamino-2-hydroxy-chroman

HRID 1453999Notes

Reaction equation

HRID 1453999 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([N:22]([CH3:24])[CH3:23])=[CH:19][CH:20]=3)[O:15][CH:14](N3CCOCC3)[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].C([O-])(O)=[O:32].[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([N:22]([CH3:24])[CH3:23])=[CH:19][CH:20]=3)[O:15][CH:14]([OH:32])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 69005398[4-(3-Bromo-4,5-dimethoxyphenyl)-2-morpholin-4-yl-chroman-7-yl]-dimethyl-amine

Product 1

HCID 100014744-(3-Bromo-4,5-dimethoxyphenyl)-7-dimethylamino-2-hydroxy-chromanYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The [4-(3-bromo-4,5-dimethoxy-phenyl)-2-morpholin-4-yl-chroman-7-yl]-dimethyl-amine was hydrolyzed to the lactol by heating 160 mg of crude solid in a mixture of acetic acid (2 ml) and water (2.4 ml) at 50° C. for 20 min. The reaction mixture was slowly added to saturated NaHCO3. It was extracted with dichloromethane (100 ml) and washed with brine (10 ml). The extract was dried over sodium sulphate and the solvent was evaporated. The crude product was passed through a bond-elute (hexane:ethyl acetate=9:1 and 4:1), yielding the title compound (110 mg; 80%). 1H NMR (CD3OD): 6.96 and 6.91 (two broad signals, 1H), 6.82 and 6.80 (two broad signals, 1H), 6.58 and 6.51 (d each, J=8.6 Hz, 1H), 6.28-6.34 (m, 1H), 6.23 and 6.22 (d each, J=2.1 Hz, 1H), 5.47 (broad signal) and 5.37 (d, J=8.9 Hz) (1H), 4.11-4.17 (m, 1H), 3.795, 3.793, 3.785 and 3.782 (s each, 6H), 2.871 and 2.868 (s each, 6H), 1.87-2.15 (m, 2H).

Workup

  1. extractionIt was extracted with dichloromethane (100 ml)
  2. washwashed with brine (10 ml)
  3. dry with materialThe extract was dried over sodium sulphate
  4. customthe solvent was evaporated
  5. washa bond-elute (hexane:ethyl acetate=9:1 and 4:1)

Sources & evidence

ORD record
ord-9499ce86b6424d81ab41015f801afb88
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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