Cyclohexylisopropylamine → HCID 23370054, compound

HRID 1900909Notes

Reaction equation

HRID 1900909 reaction equation
C1(NC(C)C)CCCCC1.C([Li])CCC.[C:16]([O:20][C:21]([CH:23]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])[C:24](O)=O)=[O:22])([CH3:19])([CH3:18])[CH3:17].[N+:32]([C:35]1[CH:42]=[CH:41][C:38](CBr)=[CH:37][CH:36]=1)([O-:34])=[O:33]>C1COCC1.CCCCCC.CN1CCCN(C)C1=O>[CH2:30]([O:29][CH2:28][CH2:27][CH:23]([CH2:24][C:38]1[CH:41]=[CH:42][C:35]([N+:32]([O-:34])=[O:33])=[CH:36][CH:37]=1)[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH3:31]

Participants

8

Reactant 4

HCID 62386CyclohexylisopropylamineHCID 660114-Nitrobenzyl bromideHCID 23370057HCID 23370057, compoundHCID 178418339Butyllithium

Product 1

HCID 23370054HCID 23370054, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclohexylisopropylamine (1.42 ml) in dry THF (3 ml) at -76° C. under argon was added a 2.5M solution of n-butyllithium in hexane (3.5 ml). The resultant solution was stirred at -76° C. for 15 minutes before a solution of the product from step (b) (1 g) in dry THF (7 ml) was added dropwise. On completion of the addition, the reaction mixture was allowed to warm to 0° C. and stirred at that temperature for 15 minutes before a solution of 4-nitrobenzyl bromide (940 mg) in dry THF (3 ml) was added, followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.5 ml). The resultant mixture was stirred at ambient temperature for 16 hours and then heated to reflux for 5 hours. The reaction mixture was evaporated to dryness and saturated ammonium chloride solution was added to the residue. The resultant mixture was extracted thoroughly with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and evaporated to give a residue which was purified by flash chromatography on silica by elution with 20% ethyl acetate/hexane to give t-butyl 2-(2-ethoxyethyl)-3-(4-nitrophenyl)propionate (940 mg) as a pale yellow oil: NMR Spectrum (CDCl3) 1.19 (3H, t), 1.33 (9H, s), 1.76 (1H, m), 1.94 (1H, m), 2.78 (1H, m), 2.91 (2H, m), 3.44 (4H, m), 7.35 (2H, d), 8.13 (2H, d); Mass Spectrum m/Z 324 (M+H)+.

Workup

  1. additionwas added dropwise
  2. additionOn completion of the addition
  3. additionwas added
  4. temperatureheated
  5. temperatureto reflux for 5 hours
  6. customThe reaction mixture was evaporated to dryness and saturated ammonium chloride solution
  7. additionwas added to the residue
  8. extractionThe resultant mixture was extracted thoroughly with ethyl acetate
  9. washthe combined extracts were washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customto give a residue which
  13. customwas purified by flash chromatography on silica by elution with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-5330c903aee546ecaf62adc81d9d6bfb
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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