Ammonium Acetate → HCID 67108736, compound

HRID 471880Notes

Reaction equation

HRID 471880 reaction equation
ClC1C=[C:4]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]3)[C:9]2=[O:19])C=CC=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:26].[Na+]>CO>[NH2:26][CH:14]1[CH2:15][CH2:16][CH2:17][C:10]2([C:9](=[O:19])[N:8]([CH3:4])[CH2:12][CH2:11]2)[CH2:13]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58237158HCID 58237158, compound

Product 1

HCID 67108736HCID 67108736, compoundYield 142.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added 2-(3-chloro-phenyl)-2-aza-spiro[4.5]decane-1,7-dione of step 5 (0.38 g, 1.35 mmol), methanol (4.92 mL), and ammonium acetate (1.25 g, 16.2 mmol). The mixture was stirred at rt for 1 hr. Sodium cyanoborohydride (0.085 g, 1.35 mmol) was then added. After stirring at rt for 2 hrs, the reaction mixture was quenched with ice and diluted with ethyl acetate (60 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 0.35 g (94%) of the title compound, 7-amino-2-methyl-2-aza-spiro[4.5]decan-1-one, as a white solid. The title compound is a mixture of two diastereomers (trans/cis: 5/2; under LC-MS method C, the first peak with RT of 0.80 min was assigned as cis, and the second peak with RT of 0.83 min was assigned as trans.). ESI-MS m/z: 279 (M+H)+. It was used without further purification.

Workup

  1. stirringAfter stirring at rt for 2 hrs
  2. customthe reaction mixture was quenched with ice
  3. additiondiluted with ethyl acetate (60 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d5f7b48efb64237a9be304f322d2435
Source dataset
uspto-grants-2014_01
Patent number
US08633190B2

Reaction notes

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