N-Methylmorpholine N-oxide monohydrate → 2-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-benzo[b]pyrano[3,2-h]-acridine-1,7(14H)-dione

HRID 478695

反応式

HRID 478695 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:25][C:24]([CH3:27])([CH3:26])[CH:23]=[CH:22][C:6]2=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[CH:13]=[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]3=[CH:10][C:9]=1[NH:8]2.[OH2:28].C[N+]1([O-])CC[O:33]CC1.OS([O-])=O.[Na+]>C(O)(C)(C)C.O1CCCC1.O.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[OH:28][CH:23]1[C:24]([CH3:27])([CH3:26])[O:25][C:5]2[C:6](=[C:7]3[C:16](=[C:3]([O:2][CH3:1])[CH:4]=2)[C:15](=[O:17])[C:14]2[CH:13]=[C:12]4[CH:18]=[CH:19][CH:20]=[CH:21][C:11]4=[CH:10][C:9]=2[NH:8]3)[C:22]1=[O:33]

参加物

7

反応物 3

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 220645146-Methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-oneHCID 23665763Sodium Bisulfite

生成物 1

HCID 220645082-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-benzo[b]pyrano[3,2-h]-acridine-1,7(14H)-dione

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 6386tert-Butanol溶媒HCID 22124471t-Butanol tetrahydrofuran water溶媒2 回

実験手順

To a solution of 1.33 mmol of the compound obtained in Step 2 in 30 ml of a 10/3/1 mixture of tert-butanol/tetrahydrofuran/water there are added osmium tetroxide in the form of a 2.5% solution in 0.67 ml of 2-methyl-2-propanol and 1.35 mmol of 4-methylmorpholine-N-oxide monohydrate. After stirring for two days at ambient temperature, NaHSO3 solution is added. After stirring for one hour, the reaction mixture is extracted with dichloromethane. The organic phase is dried, filtered and then evaporated under reduced pressure. Chromatography of the residue over silica gel (dichloromethane/methanol: 98/2) allows the expected product to be isolated.

後処理

  1. stirringAfter stirring for one hour
  2. extractionthe reaction mixture is extracted with dichloromethane
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto be isolated

出典と根拠

ORDレコード
ord-e2c95e9457c147e1acc8484d8a83ddb9
出典データセット
uspto-grants-2003_11
特許番号
US06642248B2

関連ノート

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