Sodium Carbonate → HCID 69646152, compound

HRID 1005194Notes

Reaction equation

HRID 1005194 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][N:22]([CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:21](=[O:34])[CH:20]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][N:22]([CH2:25][CH2:26][O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:21](=[O:34])[CH:20]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 86604494HCID 86604494, compound

Product 1

HCID 69646152HCID 69646152, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

20 mg (0.036 mmol) of tert-butyl (3'RS,4'RS)-3'-(naphthalen-2-ylmethoxy)-1-(2-phenoxy-ethyl)-1',2',3',4',5',6'-hexahydro-1H-[4,4']bipyridin-2-one-1'-carboxylate were dissolved in 3 ml of methylene chloride, treated with 40 mg (0.18 mmol) of anhydrous zinc bromide and stirred at room temperature for 3 hours. Thereupon, the reaction mixture was poured into aqueous sodium carbonate solution this was extracted with methylene chloride. The combined methylene chloride phases were dried over magnesium sulphate and concentrated, and the thus obtained residue was chromatographed on silica gel with a 9:1 mixture of methylene chloride and methanol as the eluent. Therefrom there were obtained 5.8 mg (35% of theory) of (3'RS,4'RS)-3'-(naphthalen-2-ylmethoxy)-1-(2-phenoxy-ethyl)-1',2',3',4',5',6'-hexahydro-1H-[4,4']bipyridin-2-one in the form of and amorphous, colourless solid; MS: 455 (M+H)+.

Workup

  1. extractionthis was extracted with methylene chloride
  2. dry with materialThe combined methylene chloride phases were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customthe thus obtained residue was chromatographed on silica gel with a 9:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-d40ac22336ce4f3b8331866be8c36e37
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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