تفاعل #47587

معادلة التفاعل

triethylsilane

triethylsilane

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

Triethylsilane

→

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

المردود 43.4%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىIn 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
   ترشيحThe mixture was filtered
5. 5
   أخرىto remove the catalyst
6. 6
   غسيلthe solids washed with methanol
7. 7
   تركيزThe filterate was concentrated in vacuo
8. 8
   أخرىazeotroped with toluene
9. 9
   workup.DISSOLUTIONdissolved in dichloromethane
10. 10
    تركيزconcentrated in vacuo with silica gel (2 g)
11. 11
    أخرىPurification by Biotage flash chromatography (Aspire 40 g column, 100% ethyl acetate)

الإجراء التجريبي

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.

المصدر