Triethylamine → HCID 67408833, compound
Reaction equation
[CH2:1]1[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][N:2]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C.[C:24](=O)([O:33]N1C(=O)CCC1=O)[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH2:1]1[C:4]2([CH2:5][CH2:6][N:7]([C:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:33])[CH2:8][CH2:9]2)[CH2:3][N:2]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate (21.0 g, 92.8 mmol) and triethylamine (20 mL, 186 mmol) were dissolved in dichloromethane (200 mL). The reaction was cooled to 0° C. and a solution of benzyl 2,5-dioxopyrrolidin-1-yl carbonate (23.1 g, 92.8 mmol) in dichloromethane (25 mL) was added dropwise. The ice-bath was removed and the reaction was stirred at room temperature for 6 hours. The reaction was diluted with dichloromethane (100 mL), washed with 10% aqueous citric acid solution (100 mL), water (100 mL) and brine (100 mL). The organic solution was dried over MgSO4, filtered and concentrated to afford 7-benzyl 2-tert-butyl 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate (33.5 g, 100%) as colorless oil, which was used in the next step without further purification.
Workup
- customThe ice-bath was removed
- additionThe reaction was diluted with dichloromethane (100 mL)
- washwashed with 10% aqueous citric acid solution (100 mL), water (100 mL) and brine (100 mL)
- dry with materialThe organic solution was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1e4a76d9f484421cb2940d69d2212d99
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609680B2
Reaction notes
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