Hexane → cis-1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]urea

HRID 2075911Notes

Reaction equation

HRID 2075911 reaction equation
[CH2:1]([Zn]CC)C.CCCCCC.ClCI.[C:15]12([CH2:25][CH2:26][N:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:28]([NH:30][CH2:31]/[CH:32]=[CH:33]\[C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[O:29])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.[Cl-].[NH4+]>ClCCCl.C(OCC)(=O)C>[C:15]12([CH2:25][CH2:26][N:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:28]([NH:30][CH2:31][C@@H:32]3[CH2:1][C@@H:33]3[C:34]3[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=3)=[O:29])[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:23]3)[CH2:22]1)[CH2:24]2

Participants

8

Reactant 5

HCID 8058HexaneHCID 11644ChloroiodomethaneHCID 25517Ammonium Chloride2×HCID 10294976(Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]ureaHCID 178418750HCID 178418750, compound

Product 1

HCID 67118730cis-1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]ureaYield 3.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M solution of diethylzinc in hexane (3.1 ml, 3.1 mmol) and chloroiodomethane (0.44 ml, 6.1 mol) were added to a solution of (Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea (Compound No. 1-111) in anhydrous 1,2-dichloroethane (3 ml) under a nitrogen atmosphere and ice-cooling, and the mixture was stirred for one hour. A saturated aqueous ammonium chloride solution (10 ml) was added to the reaction mixture under ice-cooling, and the whole was stirred at room temperature for 20 minutes and distributed with ethyl acetate (20 ml) and a saturated aqueous ammonium chloride solution (10 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 9.0 mg (3.5%) of the titled compound as colorless crystals.

Workup

  1. temperatureice-cooling
  2. temperaturecooling
  3. stirringthe whole was stirred at room temperature for 20 minutes
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4daafe821f9b42cc80272385fbf5dc91
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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