Diisopropylamine → HCID 18625922, compound

HRID 1859979Notes

Reaction equation

HRID 1859979 reaction equation
[CH2:1]([Li])[CH2:2]CC.C(NC(C)C)(C)C.[CH3:13][CH:14]([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O-:17])=[O:16].[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCCCCC.O1CCCC1>[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][C:14]([CH3:13])([CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]([O:17][CH2:1][CH3:2])=[O:16])=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 700424-Benzyloxybenzyl chlorideHCID 18625754HCID 18625754, compoundHCID 178418339Butyllithium

Product 1

HCID 18625922HCID 18625922, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of n-butyllithium in hexane (1.65M, 19.4 ml) was added dropwise over a period of 20 minutes at −60° C. to a solution of diisopropylamine (3.23 g) in anhydrous tetrahydrofuran (60 ml). The mixture was stirred at 0° C. for 30 minutes. To this mixture a solution of 2-methyl-5-phenylvalerate (7.05 g) in anhydrous tetrahydrofuran (30 ml) was added dropwise over a period of 20 minutes at −70° C. and the mixture was stirred at −70° C. for 40 minutes. To this reaction mixture a solution of 4-benzyloxybenzyl chloride (9.68 g) in anhydrous tetrahydrofuran (80 ml) was added dropwise at −70° C. The mixture was stirred at −70° C. for 3 hours. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=15/1 as the eluant to afford the desired compound (1.88 g) as a syrup.

Workup

  1. stirringthe mixture was stirred at −70° C. for 40 minutes
  2. stirringThe mixture was stirred at −70° C. for 3 hours
  3. customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-b4a8723293da4306a82f90472d25258b
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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