Methanol → HCID 54305973、化合物

HRID 1379552ノート

反応式

HRID 1379552 の反応式
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24].[C:25](=N)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CO.C([BH3-])#N.[Na+]>ClCCl.Cl.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24]

参加物

9

反応物 4

HCID 887MethanolHCID 136809Benzophenone imineHCID 5003444Sodium cyanoborohydrideHCID 54238570HCID 54238570、化合物

生成物 1

HCID 54305973HCID 54305973、化合物収率 83%

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 313Hydrochloric Acid触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (22 mg, 0.07 mmol), in 0.25 mL of dichloromethane was added benzophenone imine (1 eq), followed by 1 drop of 1N hydrochloric acid. The mixture was stirred at room temperature for 1 h, concentrated, and 0.5 mL of methanol and sodium cyanoborohydride (0.14 mmol) followed by two drops of glacial acetic acid was added, and the mixture was stirred for 16 h, diluted with ethyl acetate, rinsed with saturated sodium bicarbonate solution, and brine. The organic layer was dried over sodium sulfate, concentrated and chromatographed on silica gel (ethyl acetate eluent) to give, after trituration of the resulting oil from ether/hexanes, 28 mg (83%) of the title compound as a white solid. mp 109°-111°. FDMS: m/e=486. α[D]589 =+46.90 (c=0.49, methanol).

後処理

  1. concentrationconcentrated
  2. additionwas added
  3. stirringthe mixture was stirred for 16 h
  4. washrinsed with saturated sodium bicarbonate solution, and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed on silica gel (ethyl acetate eluent)
  8. customto give

出典と根拠

ORDレコード
ord-c2bc49d4c8f249e28056fb4628ce3df3
出典データセット
uspto-grants-1997_09
特許番号
US05670514

反応ノート

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