تفاعل #462665

معادلة التفاعل

potassium carbonate

N-butoxymethyl-N-trimethylsilylmethylbenzylamine

3,4-dihydro-4,4-diphenyl-2H-thiapyran 1,1-dioxide

N-butoxymethyl-N-trimethylsilylmethylbenzylamine

→

(4aRS,7aRS)-6-benzyl4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1,1-dioxide

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture is stirred for 2 hours at 35° C
2. 2
   workup.STIRRINGafter stirring for 1 hour
3. 3
   ترشيحThe suspension is filtered
4. 4
   تركيزthe filtrate concentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   أخرىThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.2 cm, height 35 cm)
6. 6
   غسيلeluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume)
7. 7
   أخرىcollecting fractions of 30 cm3
8. 8
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)

الإجراء التجريبي

2 drops of trifluoroacetic acid are added to a solution of 1.3 g of 3,4-dihydro-4,4-diphenyl-2H-thiapyran 1,1-dioxide and 1.75 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 12 cm3 of anhydrous dichloromethane, and the mixture is stirred for 30 minutes at 30° C. 1.75 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine and 2 drops of trifluoroacetic acid are again added and the mixture is stirred for 2 hours at 35° C. This last procedure is once again repeated and after stirring for 1 hour, 1 g of potassium carbonate is added. The suspension is filtered and the filtrate concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.2 cm, height 35 cm), eluting under a nitrogen pressure of 0.5 bar with a cyclohexane and ethyl acetate mixture (80/20 by volume) and collecting fractions of 30 cm3. Fractions 20 to 28 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 0.7 g of (4aRS,7aRS)-6-benzyl4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1,1-dioxide is obtained in the form of white crystals; melting point 186° l C.

المصدر