Hydrogen Peroxide → 2-(3-hydroxypropyl)-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

HRID 865339ノート

反応式

HRID 865339 の反応式
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[N+:25]=[N-:26])=[CH:14][C:6]=2[C:5]1=[O:27])[CH:2]=[CH2:3].C1(C2CCCCCCCC2)BCCCCCCC1.[OH-].[Na+].OO.S([O-])([O-])(=[O:52])=S.[Na+].[Na+]>O1CCCC1.CCO>[OH:52][CH2:3][CH2:2][CH2:1][N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[N+:25]=[N-:26])=[CH:14][C:6]=2[C:5]1=[O:27]

参加物

8

反応物 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 229050032-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-oneHCID 178418648HCID 178418648、化合物

生成物 1

HCID 229049852-(3-hydroxypropyl)-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one収率 42%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (920 mg, 2.48 mmol) in tetrahydrofuran (20 mL) was treated with 9-borabicyclononane (0.5 M/THF, 10 mL, 5.00 mmol), and the mixture was stirred under argon at room temperature for 18 hours. The mixture was then cooled in an ice bath, and EtOH (5 mL) followed by 15% aqueous NaOH (10 mL) and 30% H2O2 (15 mL) were added. The mixture was stirred for 1 hour, then saturated aqueous sodium thiosulfate was added (20 mL). The solution was partitioned between ethyl acetate and brine, and the combined ethyl acetate layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel to yield 400 mg (42%) of 2-(3-hydroxypropyl)-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil; 1H NMR(CDCl3) d7.20(d, J=3 Hz, 1H), 7.04(d, J=6 Hz, 1H), 6.91(dd, J=3, 6 Hz, 1H), 3.96(t, J=6 Hz, 2H), 3.72(t, J=6 Hz, 2H), 3.61(t, J=6 Hz, 2H), 3.26(t, J=6 Hz, 2H), 3.18(t, J=6 Hz, 2H), 2.73(t, J=6 Hz, 2H), 2.02(t, J=6 Hz, 2H), 1.77(m, 4H), 1.60(m, 2H), 1.36(m, 8H).

後処理

  1. temperatureThe mixture was then cooled in an ice bath
  2. additionwere added
  3. stirringThe mixture was stirred for 1 hour
  4. customThe solution was partitioned between ethyl acetate and brine
  5. dry with materialthe combined ethyl acetate layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography over silica gel

出典と根拠

ORDレコード
ord-19b98cb123a542e3995869e53b0b2384
出典データセット
uspto-grants-1996_10
特許番号
US05565449

反応ノート

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