Benzhydrylamine → HCID 54108237, compound

HRID 1079252Notes

Reaction equation

HRID 1079252 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-54974c0300d348a1a30958aed9d53c86
Source dataset
uspto-grants-1996_08
Patent number
US05550134

Reaction notes

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