Menthol → HCID 66939725, compound

HRID 1442968Notes

Reaction equation

HRID 1442968 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:10][CH:9]1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([CH3:34])[CH2:29][CH2:28][CH:27]([CH:30]([CH3:32])[CH3:31])[CH:26](O)[CH2:25]1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH:30]([CH:27]1[CH2:28][CH2:29][CH:24]([CH3:34])[CH2:25][CH:26]1[O:22][C:21]([CH:9]1[CH2:10][C:11](=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:23])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 1254MentholHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 68537795HCID 68537795, compound

Product 1

HCID 66939725HCID 66939725, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(3-Fluoro-benzylidene)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.68 g, 8.35 mmol), 1R,2S,5R(−) menthol (1.31 g, 8.35 mmol) was added followed by dimethylaminopyridine (1.02 g, 8.35 mmol). The mixture was cooled to 0° C. and dicyclohexylcarbodiimide (1.89 g, 9.19 mmol) in dichloromethane (10 ml) was added in one portion. The mixture was warmed to room temperature stirred for 18 h. The mixture was filtered and the filtrate was washed with 1N hydrochloric acid (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml). The organics were dried over magnesium sulphate and the solvent was removed by evaporation under reduced pressure. Purification by flashmaster column chromatography eluting with heptane:ethyl acetate (12:1) yielded the title compound (1.20 g, 31%) as a colourless oil.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with 1N hydrochloric acid (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml)
  4. dry with materialThe organics were dried over magnesium sulphate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customPurification by flashmaster column chromatography
  7. washeluting with heptane:ethyl acetate (12:1)

Sources & evidence

ORD record
ord-b84a62c3864d480eb9f18053577db687
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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