반응 #705618

반응 방정식

(+)-pinanediol 1-benzyloxycarbonylamino-2-phenylethane boronate

(+)-Pinanediol (R)-1-Benzyloxycarbonylamino-2-phenylethane Boronate

boron trichloride

→

(R)-1-benzyloxycarbonylamino-2-phenylethane boronic acid

용매

CH2Cl2

반응 조건

후처리

1. 1
   농축, then concentrated under vacuum
2. 2
   세척the residue is washed with ether
3. 3
   workup.ADDITIONtreated with methanol
4. 4
   농축concentrated
5. 5
   workup.DISSOLUTIONdissolved in water
6. 6
   농축concentrated
7. 7
   기타crystallized from THF/water

실험 절차

To a solution of 2.93 g. (7 mmol) of (+)-pinanediol-1-benzyloxycarbonylamino-2-phenylethane boronate (IV) in 20 ml of CH2Cl2 at -78° C. is added 24 ml of boron trichloride. The mixture is kept at 20° C. for 2 hrs., then concentrated under vacuum and the residue is washed with ether, treated with methanol, concentrated and dissolved in water. The solution is then neutralized with Dowex 1-x8 ion exchange resin bicarbonate, concentrated and crystallized from THF/water to give (R)-1-benzyloxycarbonylamino-2-phenylethane boronic acid and its anhydride.

출처