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 1876923ノート

反応式

HRID 1876923 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-429013e3bce1449aa0a08d1c96a5881c
出典データセット
uspto-grants-2012_11
特許番号
US08309730B2

反応ノート

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