Acetic Acid → 6-[(E)-2-cyclopentyl-1-{4-[(1-ethylazetidin-3-yl)sulfanyl]phenyl}ethenyl]-2-methoxy-3-methylpyridine

HRID 70595Notes

Reaction equation

HRID 70595 reaction equation
[CH:1](=O)[CH3:2].C(O)(=O)C.[NH:8]1[CH2:11][CH:10]([S:12][C:13]2[CH:18]=[CH:17][C:16](/[C:19](/[C:26]3[N:31]=[C:30]([O:32][CH3:33])[C:29]([CH3:34])=[CH:28][CH:27]=3)=[CH:20]\[CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:15][CH:14]=2)[CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.O>[CH:21]1(/[CH:20]=[C:19](/[C:26]2[N:31]=[C:30]([O:32][CH3:33])[C:29]([CH3:34])=[CH:28][CH:27]=2)\[C:16]2[CH:15]=[CH:14][C:13]([S:12][CH:10]3[CH2:11][N:8]([CH2:1][CH3:2])[CH2:9]3)=[CH:18][CH:17]=2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67399164HCID 67399164, compound

Product 1

HCID 674012376-[(E)-2-cyclopentyl-1-{4-[(1-ethylazetidin-3-yl)sulfanyl]phenyl}ethenyl]-2-methoxy-3-methylpyridineYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

90% acetaldehyde (31 μL) and acetic acid were added to a solution of 6-{(E)-1-[4-(azetidin-3-ylsulfanyl)phenyl]-2-cyclopentylethenyl}-2-methoxy-3-methylpyridine in chloroform (2 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled and sodium triacetoxyborohydride (206 mg) was added, after which the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0→93:7) to give 6-[(E)-2-cyclopentyl-1-{4-[(1-ethylazetidin-3-yl)sulfanyl]phenyl}ethenyl]-2-methoxy-3-methylpyridine as a colorless oil (78 mg, 58%).

Workup

  1. temperatureThe reaction solution was cooled
  2. stirringafter which the mixture was stirred at room temperature for 30 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0→93:7)

Sources & evidence

ORD record
ord-9b965e5130f24e64a13e67a8468cd42e
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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