تفاعل #480986

معادلة التفاعل

2-nitrobenzenesulfonyl chloride

product

tert-butyl (3S,4S)-3-amino-4-(hydroxymethyl)-1-piperidinecarboxylate

triethylamine

→

title compound

المردود 70.0%

tert-butyl (1S,6R)-8-[(2-nitrophenyl)sulfonyl]-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

المردود 70.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice-bath was removed
2. 2
   تركيزThe mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in a mixture of ethanol and 5% aqueous NaOH (2:1, 200 mL)
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   workup.ADDITIONdiluted with ethyl acetate (200 mL)
7. 7
   أخرىthe layers were separated
8. 8
   تجفيفThe organic layer was dried over Na2SO4
9. 9
   ترشيحfiltered
10. 10
    تركيزthe filtrate concentrated under reduced pressure
11. 11
    أخرىThe residue was purified via chromatography (SiO2, 50% ethyl acetate/hexanes)

الإجراء التجريبي

The product of Example 61D (39.8 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with triethylamine (16.7 mL, 0.120 mol) followed by 2-nitrobenzenesulfonyl chloride (19.5 g, 88.0 mmol). The ice-bath was removed and the solution stirred at ambient temperature for 20 hours. The mixture was concentrated under reduced pressure and the residue dissolved in a mixture of ethanol and 5% aqueous NaOH (2:1, 200 mL). The mixture was stirred for 30 minutes, concentrated under reduced pressure, diluted with ethyl acetate (200 mL) and the layers were separated. The organic layer was dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified via chromatography (SiO2, 50% ethyl acetate/hexanes) to provide the title compound (11.0 g, 27.7 mmol, 70% yield for two steps). MS (DCI/NH3) m/z 415 (M+NH4)+.

المصدر