反応 #47587

反応方程式

triethylsilane

triethylsilane

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

Triethylsilane

→

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

収率 43.4%

溶媒

methanol

反応条件

後処理

1. 1
   その他In 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
   ろ過The mixture was filtered
5. 5
   その他to remove the catalyst
6. 6
   洗浄the solids washed with methanol
7. 7
   濃縮The filterate was concentrated in vacuo
8. 8
   その他azeotroped with toluene
9. 9
   workup.DISSOLUTIONdissolved in dichloromethane
10. 10
    濃縮concentrated in vacuo with silica gel (2 g)
11. 11
    その他Purification by Biotage flash chromatography (Aspire 40 g column, 100% ethyl acetate)

実験手順

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.

出典