Hydrochloric Acid → Hydrochloric Acid

HRID 2187945Notes

Reaction equation

HRID 2187945 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2C(OC(C)(C)C)=O)[CH:4]=1)#[N:2].[H][H].[ClH:32]>C(O)C.O1CCOCC1.[Pd]>[ClH:32].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)[CH:4]=1)#[N:2]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 69923031ethyl 3-[4-cyano-(2R)-2-(1-t-butoxycarbonylpyrrolidine-2-ylmethoxy)phenyl]acrylateHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 69922876ethyl 3-[4-cyano-(2R)-2-(pyrrolidine-2-ylmethoxy)phenyl]propionate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3.0 g (7.5 mmol) of ethyl 3-[4-cyano-(2R)-2-(1-t-butoxycarbonylpyrrolidine-2-ylmethoxy)phenyl]acrylate was dissolved in 20 ml of ethanol. 600 mg of 10% palladium/carbon (50% aqueous) was added to the obtained solution, and they were stirred in the presence of hydrogen overnight. The reaction solution was filtered through Celite, and the solvent was evaporated. The obtained crude product was dissolved in 10 ml of 4 N solution of hydrogen chloride in dioxane, and the obtained solution was stirred at room temperature for 3 hours. The solvent was evaporated to obtain hydrochloride of the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customthe solvent was evaporated
  3. customThe obtained crude product
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-81c5083225c84795999b09dcc935165f
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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