반응 #41292

반응 방정식

tert-butyl[(1S)-2-(4-ethylphenyl)-1-methyl-2-oxoethyl]carbamate

Al(iPr)3

2-propanol

→

subtitle compound

tert-Butyl[(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate

용매

toluene

반응 조건

후처리

1. 1
   온도Then the reaction mixture was cooled to r.t.
2. 2
   기타quenched with aqueous HCl (1 N, 10 ml)
3. 3
   workup.ADDITIONdiluted with ethyl acetate (10 ml)
4. 4
   기타The layers were separated
5. 5
   세척the organic layer was washed with water (80 ml)
6. 6
   건조dried with Na2SO4
7. 7
   농축concentrated

실험 절차

The procedure described by J. Yin et al., J. Org. Chem. 2006, 71, 840-843) was used. A mixture of tert-butyl[(1S)-2-(4-ethylphenyl)-1-methyl-2-oxoethyl]carbamate (555 mg, 2 mmol), Al(iPr)3 (81 mg, 0.4 mmol), 2-propanol (1.32 g, 22 mmol), and toluene (2.6 ml, 1.3 ml/mmol) was heated in a sealed vial at 50° C. overnight. Then the reaction mixture was cooled to r.t., quenched with aqueous HCl (1 N, 10 ml), and diluted with ethyl acetate (10 ml). The layers were separated, the organic layer was washed with water (80 ml), dried with Na2SO4, and concentrated. Trituration with n-heptane (30 ml) afforded the subtitle compound as colourless precipitate, 137 mg. n-Heptane solution was concentrated under reduced pressure, and the residue purified by flash chromatography in silica gel to give the second crop of the subtitle compound, 318 mg. Overall yield 455 mg (81%).

출처