Diisopropylethylamine → 1-Boc-N-(2-propyn-1-yl)azetidine-3-carboxamide
Reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C[N:17](C)[CH2:18][CH2:19][CH2:20]N=C=NCC.O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C(N)C#C>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH:10]([C:12](=[O:14])[NH:17][CH2:18][C:19]#[CH:20])[CH2:11]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To 0.5 g (2.48 mmol) boc-azetidine-3-carboxylic acid in 5 mL DCM were added 0.52 g (2.73 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.4 g (2.98 mmol) 1-hydroxybenzotriazole hydrate and 0.9 mL (5.47 mmol) DIPEA, and the reaction was stirred at room temperature for 30 minutes. 0.19 mL (2.73 mmol) propargylamine was added and the reaction was stirred for 16 hours at room temperature. 5 mL DCM was added and the mixture was washed with 10 mL aqueous HCl (1 M), then 10 mL aqueous NaHCO3 (1 M) and 10 mL brine. The organic layer was dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 7:3).
Workup
- stirringthe reaction was stirred for 16 hours at room temperature
- washthe mixture was washed with 10 mL aqueous HCl (1 M)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationAfter filtration and evaporation of the solvent the product
- customwas purified by column chromatography (silica, heptane/EtOAc 7:3)
Sources & evidence
- ORD record
- ord-35d3d9d9a17d41278b9cdac0bf2ed3e9
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346816B2
Reaction notes
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