Citric Acid → 2-((2RS,3RS)-2,3-Diethyl-4-oxoazetidin-1-yl)acetonitrile
Reaction equation
[CH2:1]([CH:3]1[CH:6]([CH2:7][CH3:8])[NH:5][C:4]1=[O:9])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:21][C:22]#[N:23].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH2:7]([CH:6]1[CH:3]([CH2:1][CH3:2])[C:4](=[O:9])[N:5]1[CH2:21][C:22]#[N:23])[CH3:8]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
(3RS,4RS)-3,4-diethylazetidin-2-one (step 2) (100 mg, 0.786 mmol) in dry THF (5 ml) was cooled to −78° C. and was treated with lithium bis(trimethylsilyl)amide (0.786 ml, 0.786 mmol) [1M in THF]. The solution was allowed to warm to 0° C. then re-cooled to 0° C. before adding bromoacetonitrile (0.060 ml, 0.865 mmol). The mixture was allowed to warm to RT overnight. 10% Aqueous citric acid (30 ml) was added and the mixture was extracted with ether (4×40 ml). The combined organic layers were dried MgSO4, filtered and evaporated to dryness. Purification by chromatography on silica eluting with 0-100% Et2O in iso-hexane afforded the title compound;
Workup
- temperaturethen re-cooled to 0° C.
- temperatureto warm to RT overnight
- extractionthe mixture was extracted with ether (4×40 ml)
- filtrationfiltered
- customevaporated to dryness
- customPurification by chromatography on silica eluting with 0-100% Et2O in iso-hexane
Sources & evidence
- ORD record
- ord-3caceca83dd84a62a610b54e6307fc82
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883819B2
Reaction notes
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