tert-Butyl bromoacetate → (S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

HRID 2388671Notes

Reaction equation

HRID 2388671 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][C@H:23]2[CH2:32][OH:33])(=[O:21])=[O:20])=[C:14]([CH3:34])[CH:13]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH3:34])[C:15]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][C@H:23]2[CH2:32][O:33][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])(=[O:20])=[O:21])=[C:16]([CH3:18])[CH:17]=1

Participants

6

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 57916293(S)-(1-(4-methoxy-2,6-dimethyl-phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methanol

Product 1

HCID 57916258(S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl 2-bromoacetate (1.358 g, 6.972 mmol) and tetra-n-butylammonium hydrogen sulfate (110 mg, 0.332 mmol) were stirred in sodium hydroxide solution (26 ml, 50% aq) and toluene (20 ml). A solution of (S)-(1-(4-methoxy-2,6-dimethyl-phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methanol (1.2 g, 3.32 mmol) in toluene (10 ml) was added slowly. The addition was exothermic, cooling was achieved with an ice bath. After stirring at room temperature for 1 h, the phases were separated and the aqueous phase was extracted with diethylether (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 5/1.

Workup

  1. additionThe addition
  2. temperaturecooling
  3. customwas achieved with an ice bath
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted with diethylether (2×50 ml)
  6. washThe combined organic phases were washed with saturated sodium chloride solution (30 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 5/1

Sources & evidence

ORD record
ord-a7672e093f01445993888101191ef59a
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…