Sodium Carbonate → HCID 69054774, compound

HRID 1727176Notes

Reaction equation

HRID 1727176 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:16][CH:15]3[N:17](C(OCC(Cl)(Cl)Cl)=O)[CH:12]([CH2:13][CH2:14]3)[CH2:11]2)=[CH:5][CH:4]=1.P([O-])([O-])(O)=O.[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:11][CH:12]3[NH:17][CH:15]([CH2:14][CH2:13]3)[CH2:16]2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 24450Potassium Phosphate, DibasicHCID 69062204HCID 69062204, compound

Product 1

HCID 69054774HCID 69054774, compoundYield 86.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,2,2-trichloroethyl 3-[(4-methoxyphenyl)sulfanyl]-8-azabicyclo[3.2.1]octane-8-carboxylate (Preparation 11, 52.7 g, 0.12 moles) in tetrahydrofuran under nitrogen was added zinc dust (20 g,) and potassium hydrogenphosphate (1 M, 125 ml). The reaction mixture was stirred for 2 h at room temperature before adding more zinc dust (30 g) followed by heating on a steam bath for 30 min. The reaction mixture was cooled to room temperature and diluted with water (1 l). Sodium carbonate was added to adjust the pH to 10. The reaction mixture was filtered and the filtrate was separated and then extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as a yellow oil (26.0 g, 84%). The oil was purified by column chromatography on silica gel (350 g) eluting with methanol:dichloromethane:0.88 ammonia solution (10:90:1) to give the product as an oil which crystallised on standing (13 g, 42%). The solid was further purified by stirring in ether and filtering to give a light yellow solid (9 g, 29%).

Workup

  1. temperatureby heating on a steam bath for 30 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was separated
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f32281496c646b8804a52323219ba58
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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