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

HRID 1951567Notes

Reaction equation

HRID 1951567 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-da65b22bc75a4ad89fc4732ef3bcbc05
Source dataset
uspto-grants-2013_03
Patent number
US08404725B2

Reaction notes

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