Hydrochloric Acid → HCID 67025715, compound

HRID 656706Notes

Reaction equation

HRID 656706 reaction equation
C1(NC2CCCCC2)CCCCC1.CCCCCC.[C:20]([O:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].Br[CH2:34][CH:35]([CH2:38][CH3:39])[CH2:36][CH3:37].Cl>C1COCC1.O>[C:20]([O:24][C:25]([C:27]1([CH2:34][CH:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7582DicyclohexylamineHCID 8058HexaneHCID 77432Pentane, 3-(bromomethyl)-HCID 11816271cyclohexanecarboxylic acid tert-butyl ester

Product 1

HCID 67025715HCID 67025715, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of dicyclohexylamine (13.19 g, 72.72 mmol) in THF (90 mL) 1.6 M n-BuLi in hexane (40.7 mL, 65.12 mmol) was added with stirring over 50 min at temperature between −20° C. and −15° C. The orange suspension was stirred 10 min at −20° C. and then warmed up to 0° C. To this suspension a solution of cyclohexanecarboxylic acid t-butyl ester (10.0 g, 54.3 mmol) in THF (30 mL) was added over 15 min at 0° C. The resulting solution was stirred 30 min at 0° C., then 1-bromo-2-ethylbutane (12.54 g, 76.0 mmol) in THF (37.5 mL) was added at the same temperature over 15 min. Stirring was continued 5 h at 0° C. and overnight at room temperature. At 5° C. cold water (25 mL) was added, followed by 2N HCl (60 mL). The white suspension was filtered and the filter cake was washed with water and toluene. The organic phase of the filtrate was washed with sat. aq. NaHCO3 and with aq. NaCl. The aqueous phases were extracted with toluene. The organic phases were combined, dried over sodium sulfate and concentrated. The crude product (12.9 g) was distilled at 60° C. (0.05 mbar) to give 7.6 g (52%) 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid t-butyl ester as a colorless oil, purity 96% (GC area). 1H-NMR (CDCl3, 400 MHz): ppm 0.81 (t, 6H), 1.12-1.60 (m, 15H), 1.48 (s, 9H), 1.95-2.05 (m, 2H).

Workup

  1. stirringThe orange suspension was stirred 10 min at −20° C.
  2. stirringThe resulting solution was stirred 30 min at 0° C.
  3. stirringStirring
  4. waitwas continued 5 h at 0° C. and overnight at room temperature
  5. filtrationThe white suspension was filtered
  6. washthe filter cake was washed with water and toluene
  7. washThe organic phase of the filtrate was washed with sat. aq. NaHCO3 and with aq. NaCl
  8. extractionThe aqueous phases were extracted with toluene
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. distillationThe crude product (12.9 g) was distilled at 60° C. (0.05 mbar)

Sources & evidence

ORD record
ord-d360aad39dcb4897932915f75d939595
Source dataset
uspto-grants-2011_12
Patent number
US08071803B2

Reaction notes

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