반응 #47587

반응 방정식

triethylsilane

triethylsilane

(S)-2-benzyloxycarbonylamino-4,4-difluoro-pentanoic acid methyl ester

Triethylsilane

→

(S)-2-amino-4,4-difluoro-pentanoic acid methyl ester

수율 43.4%

용매

methanol

반응 조건

후처리

1. 1
   기타In a flask under argon was placed
2. 2
   workup.STIRRINGthe mixture was stirred for 30 min
3. 3
   workup.STIRRINGthe mixture was stirred for 30 min
4. 4
   여과The mixture was filtered
5. 5
   기타to remove the catalyst
6. 6
   세척the solids washed with methanol
7. 7
   농축The filterate was concentrated in vacuo
8. 8
   기타azeotroped with toluene
9. 9
   workup.DISSOLUTIONdissolved in dichloromethane
10. 10
    농축concentrated in vacuo with silica gel (2 g)
11. 11
    기타Purification by Biotage flash chromatography (Aspire 40 g column, 100% ethyl acetate)

실험 절차

In a flask under argon was placed (S)-2-benzyloxycarbonylamino-4,4-difluoro-pentanoic acid methyl ester (626 mg, 2.08 mmol), methanol (8 mL) and 10% palladium on activated carbon (100 mg). Triethylsilane (3 mL) was added slowly and the mixture stirred at 25° C. for 30 min. Another portion of 10% palladium on activated carbon (100 mg) and triethylsilane (3 mL) was added and the mixture was stirred for 30 min. A third portion of 10% palladium on activated carbon (100 mg) and triethylsilane (3 mL) was added and the mixture was stirred for 30 min. The mixture was filtered to remove the catalyst and the solids washed with methanol. The filterate was concentrated in vacuo, azeotroped with toluene, dissolved in dichloromethane and concentrated in vacuo with silica gel (2 g). Purification by Biotage flash chromatography (Aspire 40 g column, 100% ethyl acetate) afforded (S)-2-amino-4,4-difluoro-pentanoic acid methyl ester (151 mg) as a clear colorless liquid.

출처