Methyl morpholine oxide → 2-[(1R,2S,3R)-2,3-dihydroxycyclohexyl]-1H-isoindole-1,3(2H)-dione

HRID 1951567노트

반응식

HRID 1951567 반응식
[C@@H:1]1([N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C[N+]1([O-])CC[O:22]CC1.CC(C)=O.[OH2:30]>[Os](=O)(=O)(=O)=O>[OH:30][C@@H:2]1[C@H:3]([OH:22])[CH2:4][CH2:5][CH2:6][C@H:1]1[N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17]

참가 물질

5

반응물 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 583696532-[(1R)-cyclohex-2-en-1-yl]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 583696512-[(1R,2S,3R)-2,3-dihydroxycyclohexyl]-1H-isoindole-1,3(2H)-dione수율 95%

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

To a suspension of 2-[(1R)-cyclohex-2-en-1-yl]-1H-isoindole-1,3(2H)-dione (18) (19.9 mmol, 4.53 g) and 4-methylmorpholine-N-oxide (60 mmol, 7.01 g) in acetone/water (4:1, 62.5 mL), osmium tetroxide (0.2 mmol, 50 mg) was added. The reaction was stirred for 4 h. The mixture was concentrated and saturated sodium sulfite (40 mL) was added. It was then promptly extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated to give the crude product as a white solid (4.94 g, 95% yield). Chiral HPLC [8.53 min]. Analytical data matched published data (Donohoe, J. T.; et al., J. Org. Chem., 2002, 67, 7946-7956)

후처리

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. additionsaturated sodium sulfite (40 mL) was added
  4. extractionIt was then promptly extracted with EtOAc three times
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-da65b22bc75a4ad89fc4732ef3bcbc05
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404725B2

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