Sodium Bicarbonate → HCID 57846917, compound

HRID 735718Notes

Reaction equation

HRID 735718 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[N:6]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:18]2[C@@H:9]([C@H:10]([C:19](OCC)=[O:20])[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=32)[CH2:8][CH2:7]1.C(=O)([O-])O.[Na+]>O1CCCC1CCO.O1CCCC1.C(OCC)(=O)C>[OH:20][CH2:19][C@H:10]1[C@H:9]2[CH2:8][CH2:7][N:6]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57846933HCID 57846933, compound

Product 1

HCID 57846917HCID 57846917, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of calcium chloride (12.5 g, 113.1 mmol) in a mixture of tetrahydrofuran-ethanol (200 ml-200 ml) was added sodium borohydride (8.5 g, 226.2 mmol) at 0° C. and the mixture was stirred for 30 min. A solution of 1-tert-butyl 4-ethyl (3aR*,4R*,9bR*)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1,4-dicarboxylate (14.6 g, 46.6 mmol) in tetrahydrofuran (50 ml) was added at 0° C., and the mixture was stirred at room temperature for 16 hrs. Saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added, and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried (over anhydrous MgSO4) and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:9, v/v) to give the title compound (326 mg, 96%) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hrs
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried (over anhydrous MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (1:9, v/v)

Sources & evidence

ORD record
ord-e17107f6183142fe919e8b02d0ade9ef
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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