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

HRID 337183ノート

反応式

HRID 337183 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 30318Osmium Tetroxide触媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-0d962995f39542ec8daa9ecf265cd1ae
出典データセット
uspto-grants-2014_11
特許番号
US08889719B2

反応ノート

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