反応 #65542

反応方程式

hydrochloric acid

water

methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate

sodium borohydride

→

2-[(4-nitrobenzyloxycarbonyl)amino]-1,3-propanediol

収率 68.7%

溶媒

ethyl acetate

tetrahydrofuran

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The organic layer was separated
3. 3
   洗浄washed with 10% aqueous sodium hydrogen carbonate and brine successively
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他evaporated
6. 6
   その他The residue was chromatographed on silica gel (160 ml)
7. 7
   洗浄eluting with a mixture of acetone and dichloromethane (1:9, V/V)

実験手順

To a solution of methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate (2.12 g) in tetrahydrofuran (20 ml) and ethanol (20 ml) was added sodium borohydride (0.54 g) at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 5 hours, to the mixture was added a mixture of concentrated hydrochloric acid (1.7 ml), water (40 ml) and ethyl acetate (40 ml). The organic layer was separated, washed with 10% aqueous sodium hydrogen carbonate and brine successively, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (160 ml) eluting with a mixture of acetone and dichloromethane (1:9, V/V) to give 2-[(4-nitrobenzyloxycarbonyl)amino]-1,3-propanediol (1.32 g).

出典