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

HRID 1488673노트

반응식

HRID 1488673 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ec30f92a43e3455ebec62c89e8c42da4
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674865

반응 노트

불러오는 중…