Hydrochloric Acid → HCID 67667820, compound

HRID 743243Notes

Reaction equation

HRID 743243 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][C@H:12]([OH:14])[CH2:11][CH:10]1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[OH:14][C@H:12]1[CH2:13][NH:9][CH:10]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57189607HCID 57189607, compound

Product 1

HCID 67667820HCID 67667820, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 173 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(4-phenylbutyl)phenoxymethyl]pyrrolidine [prepared as described in step (b) above] in 3 ml of dioxane, and the resulting mixture was allowed to stand at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was dissolved in methylene chloride. Ethyl acetate was added to the resulting solution and the mixture was allowed to stand. The crystals which precipitated were collected by filtration, to give mg (yield 74%) of the title compound as colorless crystals, melting at 135°-137° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. additionEthyl acetate was added to the resulting solution
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7e0d7127b3354d94a7f05aaad8d2463a
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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