Reaktion #700818

Reaktionsgleichung

3-(3-tert-butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)-2-cyanothiophene

hydrochloric acid

→

2-aminomethyl-3-(3-tert-butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)thiophene

Ausbeute 87.4%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto stand at ambient temperature overnight
2. 2
   Temperaturcooling
3. 3
   workup.STIRRINGthe mixture was stirred for 1 hour
4. 4
   SonstigeThe mixture was partitioned between ethyl acetate and water
5. 5
   Waschenthe separated organic layer was washed with water and brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1, V/V)

Vorschrift

A mixture of 3-(3-tert-butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)-2-cyanothiophene (471 mg) and 1M borane-tetrahydrofuran complex (3 ml) was stirred for 30 minutes at 0° C. under nitrogen atmosphere and allowed to stand at ambient temperature overnight. To the mixture was added 4N hydrochloric acid (1.5 ml) under ice-cooling, and the mixture was stirred for 1 hour. The mixture was partitioned between ethyl acetate and water, and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1, V/V) to give 2-aminomethyl-3-(3-tert-butyldiphenylsilyloxymethyl-2,4-dimethylphenyl)thiophene (415 mg) as oil.

Quelle