Hydrochloric Acid → (1S,2S,4S)-2,4-dimethylcyclohexanecarboxylic acid

HRID 401843Notes

Reaction equation

HRID 401843 reaction equation
C([C@H]1C[O:11][C:10](=[O:13])N1C(=O)/C=C/C)C1C=CC=CC=1.[CH2:19]=[CH:20][C:21](=[CH2:23])[CH3:22].[Al](Cl)(CC)CC.[C:30]1(C)[CH:35]=CC=C[CH:31]=1.Cl>C(Cl)Cl>[CH3:23][C@H:21]1[CH2:22][C@@H:30]([CH3:35])[CH2:31][CH2:19][C@@H:20]1[C:10]([OH:13])=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6557IsopreneHCID 7277Diethylaluminum chlorideHCID 5702600Locostatin

Product 1

HCID 917402(1S,2S,4S)-2,4-dimethylcyclohexanecarboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of (S,E)-4-benzyl-3-but-2-enoyloxazolidin-2-one (34.5 g, 0.14 mol) and isoprene (250 mL) in DCM was cooled to −78° C. To this solution was added a solution of Et2AlCl in toluene (100 mL, 0.18 mol) dropwise. The solution was warmed to −40° C. and stirred at this temperature overnight. 2 N HCl solution (150 mL) was added. Most of the DCM was removed under vacuum and the mixture was extracted with ether. After drying over Na2SO4, the combined organic layer was concentrated and the residue purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the desired product (39 g, 88% yield) as a crystalline white solid.

Workup

  1. customMost of the DCM was removed under vacuum
  2. extractionthe mixture was extracted with ether
  3. dry with materialAfter drying over Na2SO4
  4. concentrationthe combined organic layer was concentrated
  5. customthe residue purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-39edee807eb84cbd8306d91e7c776d56
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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