Water → HCID 22601510, compound

HRID 2308208Notes

Reaction equation

HRID 2308208 reaction equation
C(OC([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH:8]=[C:9]([C:14]1[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:16]=3[CH:15]=1)[CH2:10]2)=O)C.O.NN.[OH-].[K+].O>C(O)CO>[CH3:24][O:23][C:22]1[C:16]2[CH:15]=[C:14]([C:9]3[CH2:10][CH:11]4[NH:6][CH:7]([CH2:13][CH2:12]4)[CH:8]=3)[S:18][C:17]=2[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22601509HCID 22601509, compound

Product 1

HCID 22601510HCID 22601510, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of (±)-8-ethoxycarbonyl-3-(4-methoxybenzo[b]thiophen-2-yl)-8-azabicyclo[3.2.1]oct-2-ene (0.719 g, 2.09 mmol), hydrazine hydrate (0.51 mL, 10.4 mmol) and KOH (0.700 g, 12.5 mmol) in ethylene glycol (15 mL) was heated at reflux in a sand bath for 3 h. The reaction mixture was then cooled to room temperature and stirred overnight. The reaction mixture was poured into water (20 mL). This mixture was extracted with Et2O (3×30 mL). The combined organic layers were washed with 1.0 N HCl (1×175 mL). The layers were separated and the aqueous layer was basified with 2.5 N NaOH (25 mL). This layer was extracted with EtOAc (2×275 mL). The combined organic layers were then dried over MgSO4, concentrated, and the residue was purified by medium pressure chromatography (silica gel, 7% (10% conc. NH4OH in MeOH)/CH2Cl2] to give the intermediate title compound as an orange semi-solid (0.574 g, quantitative yield). mp (oxalate) 204-207° C. IR (KBr) 3400 (br) cm−1. Ion Spray MS 272 (M+H)+; 255 (M-16)+(base peak).

Workup

  1. temperatureat reflux in a sand bath for 3 h
  2. extractionThis mixture was extracted with Et2O (3×30 mL)
  3. washThe combined organic layers were washed with 1.0 N HCl (1×175 mL)
  4. customThe layers were separated
  5. extractionThis layer was extracted with EtOAc (2×275 mL)
  6. dry with materialThe combined organic layers were then dried over MgSO4
  7. concentrationconcentrated
  8. customthe residue was purified by medium pressure chromatography (silica gel, 7% (10% conc. NH4OH in MeOH)/CH2Cl2]

Sources & evidence

ORD record
ord-a22e0bed97b345a393e474c8269b2473
Source dataset
uspto-grants-2004_12
Patent number
US06835733B2

Reaction notes

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