1-Nitroethylene → HCID 22291221, compound
Reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li].C([Li:13])CCC.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH2:16][CH:15]2[C:22]([O:24][CH2:25][CH3:26])=[O:23].[N+:27]([CH:30]=[CH2:31])([O-:29])=[O:28]>C1COCC1>[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li+:13].[N+:27]([CH2:30][CH2:31][C:15]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16][CH:17]2[CH2:20][CH2:21][N:14]1[CH2:19][CH2:18]2)([O-:29])=[O:28]Participants
Conditions
- Temperature
- -78 °C
Procedure
Lithium diisopropylamide was prepared at 0° C. from lithium diisopropylamine (193.53 mg, 1.91 mmol) and n-butyllithium (0.764 mL, 1.91 mmol) under N2. It was added via cannula to a stirring solution of ethyl quinuclidine-2-carboxylate (320 mg, 1.74 mmol) in dry THF (10 mL) at −78° C. After 1 h, a solution of nitroethylene (140.41 mg, 1.91 mmol) in THF (5 mL) was added dropwise to the reaction mixture. After stirring for 2 h at −78° C., the reaction was quenched by adding a saturated solution of ammonium chloride (20 mL). It was extracted with ethyl acetate (5×25 mL), dried (Na2SO4), filtered and concentrated by rotary evaporation to give 325 mg (70% pure) ethyl 2-(2-nitroethyl)quinuclidine-2-carboxylate as a light brown liquid, which was taken on to the next step without further purification.
Workup
- customthe reaction was quenched
- additionby adding a saturated solution of ammonium chloride (20 mL)
- extractionIt was extracted with ethyl acetate (5×25 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-4d826b6a727449a583a091d05831df56
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956042B2
Reaction notes
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