Hydrogen Peroxide → Methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate

HRID 1714046노트

반응식

HRID 1714046 반응식
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][CH:19]=[CH:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:30].[Na+].OO>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][CH2:19][CH:18]([OH:30])[C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 68505449HCID 68505449, 화합물

생성물 1

HCID 44155800Methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

BH3Me2S (1.6 eq, 2M solution in THF) was added to a 0.2M solution of methyl 14-cyclohexyl-7,8-dihydroindolo[2,1-a][2]benzazocine-11-carboxylate in THF, and the mixture was stirred for 2 h at RT. 3M aq NaOH (3 eq) and 35% H2O2 (3 eq) were added at 0° C., and stirring was continued overnight at RT. After dilution with sat NaHCO3 the aq. phase was extracted with EtOAc, the organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give mainly methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate (with traces of its regioisomer methyl 14-cyclohexyl-6-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate).

후처리

  1. stirringstirring
  2. waitwas continued overnight at RT
  3. extractionAfter dilution with sat NaHCO3 the aq. phase was extracted with EtOAc
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d4fd2254b9ce4c0c9d2e3b130c06a432
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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