Methyl morpholine oxide → (R,R)-Hydrobenzoin

HRID 1267721

반응식

HRID 1267721 반응식
C[N+]1([O-])CC[O:5]CC1.[C:9]1(/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH2:23].CC(C)=O.C(#N)C>[O-][Os](=O)(=O)=O.O=[Os](=O)(=O)=O>[C:9]1([C@@H:15]([OH:5])[C@@H:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:23])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 3

HCID 82029Methyl morpholine oxideHCID 638088trans-StilbeneHCID 18799168Acetonitrile acetone water

생성물 1

HCID 853019(R,R)-Hydrobenzoin수율 96%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 9543328Osmate촉매

실험 절차

Resin-OsO4 (0.01 Eq. Wt.), Hydroquinidine 1,4-phthalazinediyl diether (DHQD)2PHAL (0.01 Eq. Wt.) and N-methylmorpholine-N-oxide (1.5 Eq. Wt.) were stirred in the mixed solvent of water/acetone/acetonitrile (in the volume ratio of 1:1:1). To this mixture was added trans-stilbene (1.0 Eq. Wt) and stirred at room temperature for 6 hours. After the reaction, supported osmate catalyst was filtered off and washed with methanol. The combined filtrates were concentrated under reduced pressure. The chiral ligand was recovered from the aqueous layer after acidification (1N HCl). The pure product was obtained by removing the solvent at reduced pressure followed by column chromatography. (R,R)-(+)-1,2-diphenyl-1,2-ethandiol of more than 99.0% of enantiomeric excess was obtained (yield 96%) [∝]D +92.44 (c1.0, EtOH): e.e.=99.4%

후처리

  1. customAfter the reaction
  2. filtrationwas filtered off
  3. washwashed with methanol
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customThe chiral ligand was recovered from the aqueous layer after acidification (1N HCl)
  6. customThe pure product was obtained
  7. customby removing the solvent at reduced pressure

출처 및 근거

ORD 기록
ord-259e8b4c247b4b0daa93b49d2cbaca26
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552234B1

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