تفاعل #51702

معادلة التفاعل

NaOH

(1S,4S)-5-(5-(3-thienyl)-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane

trifluoroacetic acid

→

oil

المردود 34.4%

(1S,4S)-2-(5-(3-Thienyl)-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane

المردود 34.4%

المذيبات

anisole

ظروف التفاعل

المعالجة

1. 1
   استخلاصfollowed by extraction with diethyl ether (1×15 mL)
2. 2
   أخرىto remove the anisole
3. 3
   استخلاصfollowed by extraction with diethyl ether (3×25 mL)
4. 4
   تجفيفThe combined diethyl ether extracts were dried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under vacuum
7. 7
   أخرىPurification of the residue by column chromatography on silica gel

الإجراء التجريبي

To a stirred solution of (1S,4S)-5-(5-(3-thienyl)-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.63 g, 1.4 mmol) in anisole (3.0 mL) at 0-5° C. under a nitrogen atmosphere, trifluoroacetic acid (2.0 mL, 26 mmol) was added dropwise over a 10 min period. After 0.5 h at 25° C., the solution was adjusted to pH 5 using 10% NaOH, followed by extraction with diethyl ether (1×15 mL) to remove the anisole. The aqueous portion was adjusted to pH 11 using 10% NaOH, followed by extraction with diethyl ether (3×25 mL). The combined diethyl ether extracts were dried (Na2SO4) filtered and concentrated under vacuum. Purification of the residue by column chromatography on silica gel, using chloroform:methanol:triethylamine (40:5:1) as eluent, gave a light yellow oil (124 mg, 34%).

المصدر