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Water → 6-{2-Cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-2-methoxy-3-methylpyridine

HRID 70613
Notes
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Reaction equation

HRID 70613 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[N:9]=1.CC1C=CC(S(O[CH2:35][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)(=O)=O)=CC=1.O>CCCCCC.O1CCCC1>[CH:36]1([CH2:35][CH:15]([C:10]2[N:9]=[C:8]([O:7][CH3:6])[C:13]([CH3:14])=[CH:12][CH:11]=2)[C:16]2[CH:17]=[CH:18][C:19]([S:22][CH3:23])=[CH:20][CH:21]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateHCID 584525372-Methoxy-3-methyl-6-[4-(methylsulfanyl)benzyl]pyridineHCID 178418339Butyllithium

Product 1

HCID 673994926-{2-Cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-2-methoxy-3-methylpyridine

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8058HexaneSolvent

Conditions

Temperature
-35 °C

Procedure

A solution of 2.46 M n-butyllithium in hexane (1.11 mL) was added to a solution of 2-methoxy-3-methyl-6-[4-(methylsulfanyl)benzyl]pyridine obtained in Reference Example 2-1 (400 mg) in tetrahydrofuran (5 mL) in the presence of an argon gas at −78° C., and the mixture was stirred at −35° C. for 30 minutes. The reaction solution was cooled again to −78° C. and a solution of cyclopentylmethyl 4-methylbenzenesulfonate (549 mg) in tetrahydrofuran (3 mL) was added, after which the mixture was stirred at −78° C. to 0° C. for two hours. 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 preparative TLC (hexane:ethyl acetate=19:1) to give 6-{2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethyl}-2-methoxy-3-methylpyridine as a colorless amorphous (220 mg, 42%).

Workup

  1. temperatureThe reaction solution was cooled again to −78° C.
  2. stirringafter which the mixture was stirred at −78° C. to 0° C. for two hours
  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 preparative TLC (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-40d38caecfbb4e53a943959340faf1f6
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes