تفاعل #51252

معادلة التفاعل

{4-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester

Example 1

4-[(2-{(2R)2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl }ethyl)thio]butanoic Acid

hydrochloric acid

(R)-2-methyl-CBS-oxazaborolidine

→

{4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester

المذيبات

methanol

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was warmed to room temperature
2. 2
   أخرىthe solvents were removed via reduced pressure
3. 3
   أخرىThe crude residue was purified via silica gel chromatography

الإجراء التجريبي

A solution of the {4-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester prepared as in Example 1 (250 mg, 0.71 mmol) in 10 mL of anhydrous toluene was added dropwise to a −26° C. solution of (R)-2-methyl-CBS-oxazaborolidine (Aldrich, 1 M in toluene, 0.35 mL) and borane-methyl sulfide complex (10 M, 0.07 mL). The reaction was stirred under nitrogen for 7 hours at −26° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via silica gel chromatography yielding 11 mg of {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester as an oil. This was taken directly on to the next step.

المصدر