Hydrochloric Acid → 2-(4-Acetyl-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

HRID 276305Notes

Reaction equation

HRID 276305 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[S:15][CH2:14][C:13]3([CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]2[CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:6]([CH2:25][CH3:26])[CH:5]=1)(O)=[O:2].C[Li].[CH3:29][Si](Cl)(C)C.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[S:15][CH2:14][C:13]3([CH2:16][CH2:17][CH2:18][CH2:19]3)[N:12]2[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[C:6]([CH2:25][CH3:26])[CH:5]=1)(=[O:2])[CH3:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 183162232-(4-Carboxy-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonaneHCID 178418348HCID 178418348, compound

Product 1

HCID 183163432-(4-Acetyl-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonaneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 2-(4-carboxy-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane (Method D9a; 0.046 g, 0.128 mmol) in THF (10 mL) at −78° C. was added methyllithium (1.4 M in Et2O, 0.91 mL, 1.28 mmol). The reaction mixture was while allowed to gradually warm to room temp., then was stirred overnight. Trimethylsilyl chloride (0.5 mL) was added and the mixture was stirred at room temp. for 2 h, then a 1N HCl solution (2 mL) was added. The mixture was stirred for 0.5 h, then was treated with a saturated NaHCO3 solution (10 mL). The resulting mixture was extracted with EtOAc (4×20 mL), and the combined organic layers were washed with a saturated NaCl solution (30 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative TLC (10% EtOAc/hex) to give 2-(4-acetyl-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane as a white solid (0.032 g, 73%): mp 114-115° C.

Workup

  1. temperatureto gradually warm to room temp.
  2. stirringthe mixture was stirred at room temp. for 2 h
  3. stirringThe mixture was stirred for 0.5 h
  4. extractionThe resulting mixture was extracted with EtOAc (4×20 mL)
  5. washthe combined organic layers were washed with a saturated NaCl solution (30 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative TLC (10% EtOAc/hex)

Sources & evidence

ORD record
ord-2229867fc5414608b20557f86f48978b
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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