Hydrochloric Acid → 8-amino-5-Azaspiro[3.5]nonane-5-carboxylic acid 1,1-dimethylethyl ester

HRID 1434978Notes

Reaction equation

HRID 1434978 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][C:14](=O)[CH2:13][C:9]21[CH2:12][CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:14]([NH2:24])[CH2:13][C:9]21[CH2:12][CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 17435105tert-butyl 8-oxo-5-azaspiro[3.5]nonane-5-carboxylate

Product 1

HCID 162286758-amino-5-Azaspiro[3.5]nonane-5-carboxylic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A of solution 8-Oxo-5-aza-spiro[3.5]nonane-5-carboxylic acid tert-butyl ester (Tetrahedron Letters 42, 4815 (2001)) (488 mg, 2.04 mmol) in 11 ml of MeOH was treated with ammonium acetate (1.5 g, 20.4 mmol) and sodium cyanoborohydride (100 mg, 1.6 mmol). This mixture was stirred at room temperature for 72 hours. Afterwards 0.8 ml 1N-HCl were added and stirring continued for 10 minutes. For extraction with EtOAc the solution was basified with 1N-NaOH. The crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1). Yield: 0.27 g (55%).

Workup

  1. stirringstirring
  2. waitcontinued for 10 minutes
  3. extractionFor extraction with EtOAc the solution
  4. customThe crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1)

Sources & evidence

ORD record
ord-7f81cb2e876e4885a3c88b68317a8e04
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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