Methanol → HCID 54305973, 화합물

HRID 1379552노트

반응식

HRID 1379552 반응식
[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]

참가 물질

9

반응물 4

HCID 887MethanolHCID 136809Benzophenone imineHCID 5003444Sodium cyanoborohydrideHCID 54238570HCID 54238570, 화합물

생성물 1

HCID 54305973HCID 54305973, 화합물수율 83%

시약·촉매·용매 4

HCID 176Acetic Acid촉매HCID 313Hydrochloric Acid촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c2bc49d4c8f249e28056fb4628ce3df3
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670514

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