Methanol → HCID 54305973、化合物

HRID 1682914ノート

反応式

HRID 1682914 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-cf74d340a50f4f6291555ebbe0ddd17a
出典データセット
uspto-grants-1997_06
特許番号
US05635197

反応ノート

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