Pentane → HCID 69286603, compound

HRID 2225301Notes

Reaction equation

HRID 2225301 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])C[C@H]1CC#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([Li])([CH3:32])[CH3:31].CCCCC.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>>[CH2:1]([N:8]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:43][C@H:39]1[CH2:40][C:41](=[O:42])[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8003PentaneHCID 8028TetrahydrofuranHCID 69285620HCID 69285620, compoundHCID 178506895HCID 178506895, compound

Product 1

HCID 69286603HCID 69286603, compound

Conditions

Temperature
-7 °C

Procedure

Examples 11p and 11q, Step 7: To a solution of 2-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile (0.996 g, 2.56 mmoles) in 10 ml of anhydrous THF at −78° C. was added 0.7M-isopropyl lithium in pentane (5.5 ml, 3.84 mmoles) dropwise, and the mixture was stirred for 2.5 hours while the temperature was raised to −7° C. gradually. The reaction was quenched with saturated NH4Cl and then the solution was made basic with saturated NaHCO3. It was extracted with EtOAc (2×), and the combined extracts were washed with brine, dried over Na2SO4, and evaporated to give an oily residue. It was purified by flash chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2) to give 0.73 g of 1-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-one.

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionIt was extracted with EtOAc (2×)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give an oily residue
  7. customIt was purified by flash chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-e6655e546f894ebcbee032d3d7537152
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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