Hexamethylphosphoramide → Lithium cyclohexylisopropylamide

HRID 1734707Notes

Reaction equation

HRID 1734707 reaction equation
[CH:1]1([NH:7][CH:8]([CH3:10])[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li:15])CCC.C1([Se][Se]C2C=CC=CC=2)C=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH:1]1([N-:7][CH:8]([CH3:10])[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+:15]

Participants

6

Reactant 4

HCID 12679HexamethylphosphoramideHCID 15460Diphenyl diselenideHCID 62386CyclohexylisopropylamineHCID 178418339Butyllithium

Product 1

HCID 10877271Lithium cyclohexylisopropylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium cyclohexylisopropylamide was prepared from cyclohexylisopropylamine (0.07 ml) and n-butyllithium (1.6-M, 0.265 ml) in THF (1 ml). To the resultant was added dropwise a solution of methyl ester (34) (0.1412 g) in THF (4 ml) and stirred for 2 hours. A solution of diphenyl diselenide (0.132 g) and HMPA (0.074 ml) in THF (2 ml) was added, and the mixture was stirred at -70° C. for one hour and -40° C.--30° C. for 1.5 hours. According to the conventional treatment, selenide (35) (0.1247 g) was obtained. Selenide (35) (0.1247 g) was dissolved in ethyl acetate (6 ml) and methanol (4 ml), and stirred at room temperature with aqueous hydrogen peroxide (30%) (0.5 ml) for one hour. The crude product obtained by the conventional treatment was chromatographed (ethyl acetate/hexane (1:6)) to give Δ2 -PGE2 α-methyl ester (36). Yield, 0.091 g.

Workup

  1. stirringthe mixture was stirred at -70° C. for one hour and -40° C.--30° C. for 1.5 hours

Sources & evidence

ORD record
ord-4368e7072326445a9b6f17ca861991f2
Source dataset
uspto-grants-1996_07
Patent number
US05534547

Reaction notes

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