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

반응식

HRID 478695 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 6386tert-Butanol용매HCID 22124471t-Butanol tetrahydrofuran water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e2c95e9457c147e1acc8484d8a83ddb9
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642248B2

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