Pyridine → (1R,2S,5R)-5-Methyl-N-[3-(2-methylphenoxy)propyl]-2-(propan-2-yl)cyclohexane-1-carboxamide

HRID 388176Notes

Reaction equation

HRID 388176 reaction equation
[N:1]1C=CC=C[CH:2]=1.[O:7]([CH2:14][CH2:15]N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:17]1([CH3:29])[CH2:22][CH2:21][CH:20]([CH:23]([CH3:25])[CH3:24])[CH:19]([C:26](Cl)=[O:27])[CH2:18]1.O1CCC[CH2:31]1>>[CH:23]([C@@H:20]1[CH2:21][CH2:22][C@@H:17]([CH3:29])[CH2:18][C@H:19]1[C:26]([NH:1][CH2:2][CH2:15][CH2:14][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH3:31])=[O:27])([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 156512-PhenoxyethanamineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 67299849(1R,2S,5R)-5-Methyl-N-[3-(2-methylphenoxy)propyl]-2-(propan-2-yl)cyclohexane-1-carboxamide

Procedure

In a 25 mL round bottom flask, fitted with magnetic stirrer, 10 mL of tetrahydrofurane, 6.0 mmol (1.5 eq.) of pyridine and 3.33 mmol of 2-phenoxyethanamine were added. p-Menthane carboxylic acid chloride (4.0 mmol) were added and the mixture was stirred at room temperature for 16 hours, over night. The reaction mixture was extracted with MTBE and HCl (1N in water). The organic layer was washed with NaOH (1N in water), dried over MgSO4 and concentrated. The crude product was purified by column chromatography or crystallized from MtBE and Hexane under dry ice cooling.

Workup

  1. customIn a 25 mL round bottom flask, fitted with magnetic stirrer
  2. extractionThe reaction mixture was extracted with MTBE and HCl (1N in water)
  3. washThe organic layer was washed with NaOH (1N in water)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. customcrystallized from MtBE and Hexane under dry ice cooling

Sources & evidence

ORD record
ord-594f5c5ebda648ef93722bcda216392a
Source dataset
uspto-grants-2013_02
Patent number
US08377422B2

Reaction notes

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