تفاعل #42975

معادلة التفاعل

4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

4-(4-Chloro-phenyl)-3,3-dimethyl-piperidin-4-ol

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىover 1.25 hours
2. 2
   تركيزThe mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (1.2 L)
4. 4
   غسيلwashed with aqueous sodium hydroxide (1 N, 150 mL)
5. 5
   استخلاصThe aqueous layer was extracted with additional ethyl acetate (200 mL)
6. 6
   غسيلthe combined extracts were washed with brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىThe resulting solid residue was triturated with ether

الإجراء التجريبي

To a cooled (0° C.) solution of 4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester (10.42 g, 30.7 mmol) in methylene chloride (300 mL) was slowly added trifluoroacetic acid (60 mL) over 1.25 hours. The resulting yellow solution was stirred at 0° C. for an additional 1.5 hours. The mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate (1.2 L), and washed with aqueous sodium hydroxide (1 N, 150 mL). The aqueous layer was extracted with additional ethyl acetate (200 mL) and the combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting solid residue was triturated with ether to afford 4-(4-Chloro-phenyl)-3,3-dimethyl-piperidin-4-ol as an off-white solid.

المصدر