Diisopropylamine → Methyl alpha-Cyclopentyl-1-Hydroxycyclohexaneacetate

HRID 704696Notes

Reaction equation

HRID 704696 reaction equation
C(NC(C)C)(C)C.[CH:8]1([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C1COCC1.CCCCCC>[CH:8]1([CH:13]([C:18]2([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 7967CyclohexanoneHCID 12512040Methyl 2-cyclopentylacetate

Product 1

HCID 15158222Methyl alpha-Cyclopentyl-1-HydroxycyclohexaneacetateYield 100.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

Diisopropylamine (12.7 g, 0.125) was dissolved in 150 mls of dry THF and cooled to -70° C. under N2. n-Bulb (80 ml of 1.6M solution in hexane, 0.125 moles) was added and the solution stirred for 5 minutes at -70° C. Methyl cyclopentaneacetate (17 g, 0.125 mole) in 50 mls of THF was added at -70° C. over 15 minutes and the reaction was stirred at -70° C. for 15 more minutes. A solution of cyclohexanone (11.3 g, 0.115 moles) in THF (50ml) was then added at -70° C. over 1/2 hour and stirred in the cold for 1 hour. The reaction was warmed to room temperature over 1 hour and quenched with 5 mls of 1N HCl. The solvent was removed on the rotary evaporator and ethyl acetate added. The solution was then washed with saturated NaHCO3 and the layers were separated. The organic layer was dried over Na2SO4. The drying agent was filtered and the filtrate stripped to give a residue which was chromatographed on silica gel using 7% ethyl acetate/hexane to give 27.8 g (92% yield) of the title compound.

Workup

  1. stirringthe reaction was stirred at -70° C. for 15 more minutes
  2. stirringstirred in the cold for 1 hour
  3. temperatureThe reaction was warmed to room temperature over 1 hour
  4. customquenched with 5 mls of 1N HCl
  5. customThe solvent was removed on the rotary evaporator and ethyl acetate
  6. additionadded
  7. washThe solution was then washed with saturated NaHCO3
  8. customthe layers were separated
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationThe drying agent was filtered
  11. customto give a residue which
  12. customwas chromatographed on silica gel using 7% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ae5392b57f2641f68324fe4a4718279b
Source dataset
uspto-grants-1991_01
Patent number
US04988707

Reaction notes

Loading…