Trifluoroacetic acid → 7-Methyl-2,7-diazaspiro[3.5]nonane

HRID 2066496Notes

Reaction equation

HRID 2066496 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][N:14]1[CH2:15][CH2:16][C:10]2([CH2:11][NH:8][CH2:9]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668709512,7-Diazaspiro[3.5]nonane-2-carboxylic acid, 7-methyl-, 1,1-dimethylethyl ester

Product 1

HCID 109971177-Methyl-2,7-diazaspiro[3.5]nonaneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester hydrochloride (100 mg, 0.381 mmol) in DCE (10 mL) was added an aqueous solution of formaldehyde (37% w/w, 40 μL, 0.537 mmol). The mixture was stirred at RT for 10 min, then sodium triacetoxyborohydride (121 mg, 0.571 mmol) was added and stirring was continued for 1 h. Water was added to the reaction mixture before being loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH then eluted with 2 M NH3 in MeOH to give 7-methyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester. To a solution of 7-methyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester in DCM (5 mL) was added TFA (1 mL) and the resulting mixture was stirred at RT for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH to give the title compound as a colourless oil (45 mg, 84%).

Workup

  1. washwashed with MeOH
  2. washthen eluted with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-ac94a00bf66746c080d250bae4850070
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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