(+-)-Methionine → [2-(3-Hydroxybenzyl)cyclohexyl]methyl acetate

HRID 2389376Notes

Reaction equation

HRID 2389376 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=1)(=[O:3])[CH3:2].NC(C(O)=O)CCSC.CS(O)(=O)=O.C(OCC)C>O>[C:1]([O:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 876(+-)-MethionineHCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 68535645[2-(3-Methoxybenzyl)cyclohexyl]methyl acetate

Product 1

HCID 68537998[2-(3-Hydroxybenzyl)cyclohexyl]methyl acetateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction mixture of [2-(3-methoxybenzyl)cyclohexyl]methyl acetate (66 mg), DL-methionine (357 mg), and methanesulfonic acid (1.55 mL) was stirred at ambient temperature for 18 hours. To the reaction mixture was added diethylether and water. The reaction mixture was stirred. The organic layer was washed with water, brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The mixture was purified by silica gel column chromatography (n-hexane:EtOAc=5:1) to afford [2-(3-hydroxybenzyl)cyclohexyl]methyl acetate (42 mg) as colorless oil.

Workup

  1. stirringThe reaction mixture was stirred
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe mixture was purified by silica gel column chromatography (n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-9af4b825641a4a7fb558a18e9baf2074
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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