Sodium Iodide → (R)-4-allyl-7-benzyloxy-3-(4-benzyloxyphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 460462노트

반응식

HRID 460462 반응식
[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:12]2[NH:13][C@H:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:19][CH:18]=3)[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:41](Br)[CH:42]=[CH2:43]>CC(C)=O.C(OCC)(=O)C.CCCCCC.O>[CH2:43]([N:13]1[C:12]2[CH:31]=[CH:32][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[O:16][CH2:15][C@H:14]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][CH:18]=1)[CH:42]=[CH2:41]

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 20726824(R)-7-benzyloxy-3-(4-benzyloxyphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine

생성물 1

HCID 20726823(R)-4-allyl-7-benzyloxy-3-(4-benzyloxyphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine수율 85%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A solution of (R)-7-benzyloxy-3-(4-benzyloxyphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine (47.6 mg, 0.112 mmol), sodium iodide (67 mg, 0.450 mmol), potassium carbonate (31 mg, 0.224 mmol) and allyl bromide (0.04 ml, 0.473 mmol) in acetone (1 ml) was stirred for 3 hours at 50° C. under a nitrogen stream and then heated under reflux for 7 hours. After cooling, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5, v/v) to give (R)-4-allyl-7-benzyloxy-3-(4-benzyloxyphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine (44 mg, Yield 85%).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter cooling
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-c9fcdc313af04cbb8cb4a4a78be44d09
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196081B2

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