Acetyl chloride → tert-Butyl 7-acetyl-2,7-diazaspiro[3.5]nonane-2-carboxylate

HRID 2066497Notes

Reaction equation

HRID 2066497 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23282935tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate

Product 1

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

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-7a99159f8c424b02a9fd3979966cbe07
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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