Hexamethylphosphoramide → Lithium cyclohexylisopropylamide

HRID 1461014Notes

Reaction equation

HRID 1461014 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-7dfd0b5c65114679b304809160b6727a
Source dataset
uspto-grants-1991_12
Patent number
US05073569

Reaction notes

Loading…