Benzyl chloroformate → 2-Benzyl 7-(tert-butyl) 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate

HRID 70791Notes

Reaction equation

HRID 70791 reaction equation
[OH-].[Na+].Cl[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:14]([C:16]1([CH2:29]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)#[N:15]>O1CCOCC1>[CH2:29]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:14][N:15]1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 866770551,1-Dimethylethyl 4-cyano-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-1-piperidinecarboxylate

Product 1

HCID 712686312-Benzyl 7-(tert-butyl) 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylateYield 85.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under ice-cooling, 1M sodium hydroxide aqueous solution (6.0 ml) and benzyl chloroformate (1.03 g) were sequentially added to a dioxane (50 ml) suspension of tert-butyl 4-cyano-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (2.15 g), and stirring was performed at room temperature for 16 hours. The reaction liquid was concentrated under reduced pressure, and extracted with EtOAc. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain 2-benzyl 7-tert-butyl 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate (1.68 g).

Workup

  1. temperatureUnder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-8e4cd38ad5d341e59ca3b59df05cafe4
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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