تفاعل #1985759

معادلة التفاعل

1-(3-Bromophenyl)-3,3-dimethyl-pyrrolidine

tert-Butyl lithium

2-Isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

→

3,3-dimethyl-1-[3 (4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine

المردود 75.4%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction was stirred at −78° C. for 2 h
2. 2
   أخرىThe reaction was quenched with saturated aqueous ammonium chloride
3. 3
   درجة الحرارةwarmed to room temperature
4. 4
   workup.ADDITIONWater was added
5. 5
   أخرىthe layers were separated
6. 6
   استخلاصThe aqueous layer was back extracted twice with ethyl acetate
7. 7
   أخرىThe combined organic layers were dried
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىThe crude product was chromatographed

الإجراء التجريبي

1-(3-Bromophenyl)-3,3-dimethyl-pyrrolidine (6.7 g, 26.4 mmol) was suspended in 132 ml of THF and cooled to −78° C. in a dry ice acetone bath. tert-Butyl lithium (1.7 M solution in pentane, 46.6 ml, 79.2 mmol) was added dropwise and the reaction was stirred at −78° C. for 15 min. 2-Isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (10.8 ml, 52.8 mmol) was added and the reaction was stirred at −78° C. for 2 h. The reaction was quenched with saturated aqueous ammonium chloride and warmed to room temperature. Water was added and the layers were separated. The aqueous layer was back extracted twice with ethyl acetate. The combined organic layers were dried, filtered and concentrated. The crude product was chromatographed using a gradient of 0% to 10% ethyl acetate in hexanes to give 6.0 g (75%) of 3,3-dimethyl-1-[3 (4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine.

المصدر