تفاعل #357743

معادلة التفاعل

tert-butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate

thionyl chloride

→

desired product

tert-Butyl 4-[2-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with ice water
2. 2
   استخلاصThe resulting solution was extracted with methylene chloride three times
3. 3
   تجفيفThe combined extracts were dried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification by flash chromatography on silica gel (0-40% B over 25 min

الإجراء التجريبي

To a solution of tert-butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate (0.75 g, 2.2 mmol) in pyridine (15 mL) cooled in an ice bath was slowly added thionyl chloride (0.79 mL, 11 mmol) and the mixture was warmed to room temperature and stirred overnight (17 h). The reaction was quenched with ice water. The resulting solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-40% B over 25 min. Bottle A=hexanes, Bottle B=EtOAc) gave 209 g of the desired product as a solid. MS calculated for C17H20F3NO2: (M+H) 328; found 228.0 (M-Boc+H).

المصدر