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

HRID 1582811ノート

反応式

HRID 1582811 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-18810bc05e7646579a807e93b97b12f2
出典データセット
uspto-grants-2004_05
特許番号
US06737417B2

反応ノート

読み込み中…