Hydrochloric Acid → HCID 12070578, compound

HRID 2084744Notes

Reaction equation

HRID 2084744 reaction equation
[CH2:1]1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1.C([Li])(CC)C.[CH:23]([N:26]([CH:39]([CH3:41])[CH3:40])[C:27](=[O:38])[O:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])([CH3:25])[CH3:24].CI.Cl>C(OCC)C.C1CCCCC1.O>[CH:39]([N:26]([CH:23]([CH3:24])[CH3:25])[C:27](=[O:38])[O:28][CH:29]([CH3:1])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])([CH3:41])[CH3:40]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 644020SparteineHCID 12070577HCID 12070577, compoundHCID 178418400CID 53628100

Product 1

HCID 12070578HCID 12070578, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 14.1 g (60.2 mmol) of (−)-Sparteine in 75 ml of diethyl ether was cooled to −78° C. and a 1.0M solution of 60.2 ml (60.2 mmol) of s-butyllithium in cyclohexane was added dropwise. The reaction mixture was stirred for 15 min and then added to a solution of 10 g (40.1 mmol) of 2-(2-fluorophenyl)ethyl diisopropylcarbamate in diethyl ether at −78° C. After stirring for 4 hr, methyl iodide was added, followed by stirring for 2 hr. Water was added and the resulting mixture was warmed to room temperature. The mixture was treated with 1 N—HCl, extracted 3 times with ethyl acetate, washed with water and brine and then dried over sodium sulfate. After the solvent was distilled off, purification of the residue by silica gel column chromatography gave 5.11 g of the title compound. (Yield: 45%).

Workup

  1. stirringAfter stirring for 4 hr
  2. stirringby stirring for 2 hr
  3. extractionextracted 3 times with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. custompurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-a3e40e9d9f0148fd9625c8177dfb3eb0
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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