Methanol → HCID 54305973, compound

HRID 1079238Notes

Reaction equation

HRID 1079238 reaction equation
[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]

Participants

9

Reactant 4

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

Product 1

HCID 54305973HCID 54305973, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d5ddc8eb7b444fd85310abe4dad7f18
Source dataset
uspto-grants-1996_08
Patent number
US05550134

Reaction notes

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