Benzhydrylamine → HCID 54108237, compound

HRID 1780521Notes

Reaction equation

HRID 1780521 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25].[CH:26]([NH2:39])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:39][CH:26]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25]

Participants

8

Reactant 3

HCID 7036BenzhydrylamineHCID 5003444Sodium cyanoborohydrideHCID 54402920HCID 54402920, compound

Product 1

HCID 54108237HCID 54108237, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of (+)-(4aR)-(10bR)-4-methyl-8-(3-formylphenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (30 mg, 0.09 mmol), in 0.75 mL of methanol was added benzhydryl amine (0.09 mmol), sodium cyanoborohydride (0.09 mmol) and 2 drops of glacial acetic acid (mixture became homogeneous; pH =4). The reaction was stirred at room temperature for 60 h. The mixture was diluted with ethyl acetate, saturated aqueous sodium bicarbonate solution was added, and the resulting mixture was extracted repeatedly with ethyl acetate. The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent), followed by trituration of the resulting oil with ether/hexanes, to give 36 mg (80%) of the title compound as a white solid. mp 55°-57°. FDMS: m/e=500. α[D]589 =+48.40 (c=0.64, methanol).

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted repeatedly with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (ethyl acetate eluent)

Sources & evidence

ORD record
ord-3478b18d5adb408080631c26940c5d5d
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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