Trifluoroacetic acid → 1-(2,7-Diazaspiro[3.5]nonan-7-yl)ethanone

HRID 2066498Notes

Reaction equation

HRID 2066498 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:9]1[C:10]2([CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]2)[CH2:11][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66870873tert-Butyl 7-acetyl-2,7-diazaspiro[3.5]nonane-2-carboxylate

Product 1

HCID 668703291-(2,7-Diazaspiro[3.5]nonan-7-yl)ethanoneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester (70 mg, 0.309 mmol) in DCM (3 mL) were added acetyl chloride (32 μL, 0.450 mmol) and triethylamine (54 μL, 0.526 mmol). The resulting mixture was stirred at RT for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, and washed with MeOH then eluted with 2 M NH3 in MeOH to give 7-acetyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester. To a solution of 7-acetyl-2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester in DCM (3 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 (41 mg, 79%).

Workup

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

Sources & evidence

ORD record
ord-f8ce6d7b82094f8f847f0c45e06a1466
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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