Hydride → (3-Methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol

HRID 1297700Notes

Reaction equation

HRID 1297700 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)C.[H-].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH3:19][S:16]([C:10]1[CH:11]=[N:12][C:13]2[C:8]([C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 166653HydrideHCID 21225700Diisobutylaluminumhydride2×HCID 58585876HCID 58585876, compound

Product 1

HCID 58585810(3-Methanesulfonyl-4-phenyl-quinolin-6-yl)-methanolYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

3-Methanesulfonyl-4-phenyl-quinoline-6-carboxylic acid ethyl ester (example 61g, 100 mg, 0.28 mmol) in anhydrous tetrahydrofuran (8 mL) was cooled to 0° C. First portion of diisobutylaminum hydride in THF (1 M, 930 uL, 0.93 mmol) was added to the above mixture, and the reaction went for 1 hr at about room temperature. Then the reaction was cooled to 0° C., and second portion of diisobutylaluminum hydride in THF (1 M, 930 uL, 0.93 mmol) was added. The reaction continued for another 45 min at about room temperature. The completion of the reaction was monitored using LC-MS. Additional portion of diisobutylaluminum hydride in THF (1 M, 620 uL, 0.62 mmol) was added, and the reaction went for another 30 min. The reaction was quenched with saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic solution was filtered through a bed of celit with ethyl acetate. The filtrate was collected, washed with water, brain, dried over sodium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 60% ethyl acetate in hexane in 10 min, then 60%-100% ethyl acetate in hexane in 13 min) afforded (3-methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol (70 mg, 79%). LC-MS m/e 314 (MH+).

Workup

  1. waitThe reaction continued for another 45 min at about room temperature
  2. waitthe reaction went for another 30 min
  3. customThe reaction was quenched with saturated sodium bicarbonate solution
  4. extractionfollowed by extraction with ethyl acetate
  5. filtrationThe organic solution was filtered through a bed of celit with ethyl acetate
  6. customThe filtrate was collected
  7. washwashed with water, brain
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. waitFlash chromatography (Merck Silica gel 60, 70-230 mesh, 60% ethyl acetate in hexane in 10 min

Sources & evidence

ORD record
ord-451030bb92a84ba0b16126e6e7baaaad
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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