Trifluoroacetic acid → 3-Methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl ester

HRID 1912394Notes

Reaction equation

HRID 1912394 reaction equation
C(OC([N:8]1[CH2:27][CH2:26][CH2:25][C:10]2([N:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:12][CH:11]2[CH3:24])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([N:13]1[C:10]2([CH2:25][CH2:26][CH2:27][NH:8][CH2:9]2)[CH:11]([CH3:24])[CH2:12]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 582933041-Benzyl6-tert-butyl3-methyl-1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

Product 1

HCID 582933243-Methyl-1,6-diazaspiro[3,5]nonane-1-carboxylic acid 1-benzyl esterYield 189%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of an optically-active compound of 3-methyl-1,6-diazaspiro[3,5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester (78 mg) in chloroform (2 ml) cooled to 4° C. was added trifluoroacetic acid (0.4 ml), and the mixture was warmed to room temperature and stirred for additional 1 hour. The reaction mixture was basified by the addition of 1M aqueous sodium hydroxide solution, and extracted with chloroform. The separated organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (108 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe separated organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2820a1e91be43fcbdb198071a7af4c0
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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