Hydrochloric Acid → HCID 9822797, compound

HRID 1815433Notes

Reaction equation

HRID 1815433 reaction equation
[C:1]([O:4][CH:5]1[C:12]2[N:8]([C:9]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:6]1([CH3:35])[CH3:34])(=O)C.[OH-].[K+].O.Cl>CO>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:10]2[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:12]3[N:8]([CH2:7][C:6]([CH3:34])([CH3:35])[CH:5]3[O:4][CH3:1])[C:9]=2[CH2:26][C:27]([OH:29])=[O:28])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 9913642HCID 9913642, compound

Product 1

HCID 9822797HCID 9822797, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 1-acetoxy-6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-ylacetate (example 9c, 1.00 g, 2.0 mmol) is dissolved in 10 ml of MeOH. 0.5 g of KOH is added and the mixture is heated under reflux until the intermediately formed precipitate has dissolved. It is then allowed to cool and is stirred into 600 ml of water. The cloudy solution is brought to pH 3 using conc. HCl. It is extracted three times using 100 ml of diethyl ether each time. The ether extracts are washed twice with water and dried over Na2SO4, filtered and concentrated in a rotary evaporator. A mixture of 6-(4-chlorophenyl)-2,3-dihydro-1-hydroxy-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-ylacetic acid and 2-[6-(4-chlorophenyl)-2,3-dihydro-1-methoxy-2,2-dimethyl -7-phenyl-1H-pyrrolizin-5-yl]acetic acid is obtained (cf. example 16).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux until the intermediately formed precipitate
  3. dissolutionhas dissolved
  4. temperatureto cool
  5. extractionIt is extracted three times
  6. washThe ether extracts are washed twice with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in a rotary evaporator
  10. additionA mixture of 6-(4-chlorophenyl)-2,3-dihydro-1-hydroxy-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-ylacetic acid

Sources & evidence

ORD record
ord-62958335183e491f91dcd41935a479d3
Source dataset
uspto-grants-2005_04
Patent number
US06878738B1

Reaction notes

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