Sodium Bicarbonate → HCID 86686757, compound

HRID 1403123Notes

Reaction equation

HRID 1403123 reaction equation
O=[C:2]1[CH2:22][CH2:21][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.C([O-])(=O)C.[NH4+:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[NH2:27][CH:2]1[CH2:22][CH2:21][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 59803011Benzyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 86686757HCID 86686757, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (230 mg) was dissolved in methanol (4.5 mL) and methylene chloride (1.5 mL), and ammonium acetate (1.47 g) was added thereto, followed by stirring at room temperature for 10 minutes. Subsequently, sodium triacetoxyborohydride (323 mg) was added thereto, followed by stirring at room temperature overnight. To the reaction solution was added saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain benzyl 9-amino-3-azaspiro[5.5]undecane-3-carboxylate (255 mg).

Workup

  1. stirringby stirring at room temperature overnight
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2d43438cfa642d0b9c37a7d63b9aadb
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…