Thiophenol → HCID 67578873, compound

HRID 1584740Notes

Reaction equation

HRID 1584740 reaction equation
[CH3:1][N:2]1[CH:6]2[C:7]([C:10]([OH:12])=[O:11])=[CH:8][CH2:9][CH:3]1[CH2:4][CH2:5]2.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20]CN(CC)CC>C(Cl)(Cl)Cl>[CH3:20][O:11][C:10]([C@@H:7]1[C@H:8]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:3]2[N:2]([CH3:1])[C@@H:6]1[CH2:5][CH2:4]2)=[O:12]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 1017098-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid

Product 1

HCID 67578873HCID 67578873, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A nitrogen purged 0° C. solution of methylester of anhydroecgonine (2.008 g, 11.08 mmol) and thiophenol (2.9 mL, 3.05 g, 27.7 mmol) in chloroform (100 mL) was treated with Et3N (0.55 mL) and stirred at room temperature for 24 h. The mixture was then concentrated on a rotary evaporator, diluted with Et2O (50 mL) and washed twice with 0.1N NaOH (3×20 mL). The organic layer was dried (Na2SO4), decanted and concentrated on a rotary evaporator. The residue was purified by flash chromatography (20% Et3N/Et2O) to afford 3α(phenylthio)tropane-2a-carboxylic acid methyl ester as a very pale yellow oil (319 mg, 10%) contaminated with the starting material (5% of 319 mg).

Workup

  1. concentrationThe mixture was then concentrated on a rotary evaporator
  2. additiondiluted with Et2O (50 mL)
  3. washwashed twice with 0.1N NaOH (3×20 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customdecanted
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was purified by flash chromatography (20% Et3N/Et2O)

Sources & evidence

ORD record
ord-5d03cf01f36b46f79e87609cbb50b514
Source dataset
uspto-grants-1999_08
Patent number
US05935953

Reaction notes

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