Acetonitrile → 2-(2-Ethyl-4-(2-cyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane
Reaction equation
[OH-].[K+].[CH2:3]([C:5]1[CH:10]=[C:9]([CH:11]=O)[CH:8]=[CH:7][C:6]=1[N:13]=[C:14]1[S:18][CH2:17][C:16]2([CH2:22][CH2:21][CH2:20][CH2:19]2)[N:15]1[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH3:4].[CH3:28][C:29]#[N:30]>>[CH2:3]([C:5]1[CH:10]=[C:9]([CH:11]=[CH:28][C:29]#[N:30])[CH:8]=[CH:7][C:6]=1[N:13]=[C:14]1[S:18][CH2:17][C:16]2([CH2:22][CH2:21][CH2:20][CH2:19]2)[N:15]1[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH3:4]Participants
4
Procedure
To a solution of KOH (0.024 g, 0.36 mmol) in CH3CN (20 ml) at the reflux temp. was added 2-(2-ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane (Method D11a; 0.127 g, 0.36 mmol). The reaction mixture was heated at the reflux temp. for 4 h, cooled to room temp., and concentrated under reduced pressure The residue was diluted with water (15 mL) and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with a saturated NaCl solution and dried (Na2SO4). The resulting material was purified by preparative TLC (30% EtOAc/hex) to give 2-(2-ethyl-4-(2-cyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane as 1:3 cis/trans mixture of isomers (0.050 g): TLC (30% EtOAc/hex) Rf0.56.
Workup
- temperatureThe reaction mixture was heated at the reflux temp
- temperaturecooled to room temp.
- concentrationconcentrated under reduced pressure The residue
- additionwas diluted with water (15 mL)
- extractionextracted with CH2Cl2 (3×15 mL)
- washThe combined organic layers were washed with a saturated NaCl solution
- dry with materialdried (Na2SO4)
- customThe resulting material was purified by preparative TLC (30% EtOAc/hex)
Sources & evidence
- ORD record
- ord-ec40e79df669453585dfd5809d0b45a5
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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