Hydrochloric Acid → HCID 86754981, compound

HRID 612851Notes

Reaction equation

HRID 612851 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)C1C=CC=CC=1.[ClH:24].[H][H]>[C].[Pd].C(O)C>[ClH:24].[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([S:14]([O:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10471906Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86754981HCID 86754981, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixed solution obtained by mixing 3.0 g of 100% pure (R)-1-benzyl-3-p-toluenesulfonyloxypyrrolidine with 3.0 ml of ethanol and adding dropwise 0.80 ml of 35% aqueous hydrochloric acid thereto with cooling on an ice-water bath was charged, together with 150 mg of moist 5% palladium-carbon (water content 52% by weight), into an autoclave, hydrogen was introduced thereinto and the autoclave was heated to raise the temperature to 60 and the pressure to 203 kPa, and the reaction was allowed to proceed for 4.5 hours. Hydrogen absorption came to an end in 2.5 hours after the start of hydrogen introduction. After completion of the reaction, the reaction mixture was treated in the same manner as in Example 4 to give 2.51 g (yield: 86 mole percent) of (R)-3-p-toluenesulfonyloxypyrrolidine hydrochloride.

Workup

  1. customA mixed solution obtained
  2. temperaturewith cooling on an ice-water bath
  3. additionwas introduced
  4. temperaturethe autoclave was heated
  5. temperatureto raise the temperature to 60
  6. customHydrogen absorption
  7. waitcame to an end in 2.5 hours
  8. customAfter completion of the reaction
  9. additionthe reaction mixture was treated in the same manner as in Example 4

Sources & evidence

ORD record
ord-af582adf6d6841b886138afea909c74d
Source dataset
uspto-grants-1999_12
Patent number
US06005119

Reaction notes

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