Sodium Thiosulfate → ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate

HRID 1876923노트

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HRID 1876923 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:34])([C@@H:14]([CH:21]([OH:33])[C:22]4[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=4)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:34])([C@@H:14]([C:21]([C:22]4[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=4)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:33])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67447028ethyl 3-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)benzoate

생성물 1

HCID 67445249ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

The above ethyl 3-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)benzoate was dissolved in anhydrous methylene chloride (5 mL). Pyridine (0.1 mL) and Dess-Martin periodinane (215 mg, 0.51 mmol) were added. The reaction mixture was stirred at RT for 40 min before saturated aqueous sodium bicarbonate solution (6 mL) and saturated aqueous sodium thiosulfate solution (3 mL) were added. The mixture was stirred at RT for 20 min. The aqueous layer was separated and extracted with methylene chloride (2×2 mL). The combined organic solutions were dried (Na2SO4). Silica gel flash chromatography (20-100% ethyl acetate in heptanes, then 0-20% methanol in ethyl acetate) gave ethyl 3-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)benzoate as a solid.

후처리

  1. additionwere added
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride (2×2 mL)
  4. dry with materialThe combined organic solutions were dried (Na2SO4)

출처 및 근거

ORD 기록
ord-429013e3bce1449aa0a08d1c96a5881c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309730B2

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