تفاعل #57059

معادلة التفاعل

(S)-2-methyl-CBS-oxazaborolidine

Methyl 4-{2-[(2R)-2((1E,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-oxooct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

→

Methyl 4-{2-[(2R)-2((1E,3R,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 3 hours
2. 2
   أخرىThe mixture was quenched with addition of 1 mL of the saturated ammonia chloride
3. 3
   workup.ADDITIONwas dilute with EtOAc (20 mL)
4. 4
   غسيلThe organic layer was washed with brine (3×5 mL)
5. 5
   تجفيفdried over MgSO4
6. 6
   أخرىThe residue was used for the next reaction without purification

الإجراء التجريبي

To a solution of (S)-2-methyl-CBS-oxazaborolidine (1.0 M in toluene, 0.4 mL, 0.4 mmol) in anhydrous THF (10 mL) at 0° C. was added Borane-THF complex (1.0 M, 0.4 mL, 0.4 mmol) dropwise. The mixture was stirred for 15 minutes. Methyl 4-{2-[(2R)-2((1E,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-oxooct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate (200 mg, 0.4 mmol) in THF (1 mL) was added dropwise. The mixture was stirred for 3 hours. The mixture was quenched with addition of 1 mL of the saturated ammonia chloride and was dilute with EtOAc (20 mL). The organic layer was washed with brine (3×5 mL), dried over MgSO4. The residue was used for the next reaction without purification.

المصدر