Hydrochloric Acid → HCID 67669462, compound

HRID 743317Notes

Reaction equation

HRID 743317 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[C:24]1([CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C@H:10]2[CH2:11][CH2:12][CH2:13][NH:9]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54336094HCID 54336094, compound

Product 1

HCID 67669462HCID 67669462, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 630 mg of (R)-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in step (a) above] in 5 ml of dioxane, and the resulting mixture was allowed to stand at room temperature for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting oily residue was cooled, which resulted in its solidification. The solid was triturated in pentane, and the resulting powder was collected by filtration to give 360 mg (yield 68%) of the title compound as a colorless solid, melting 73°-88° C. [α]D25 -7.5° (c=3.76, ethanol).

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. temperaturethe resulting oily residue was cooled
  3. customwhich resulted in its solidification
  4. customThe solid was triturated in pentane
  5. filtrationthe resulting powder was collected by filtration

Sources & evidence

ORD record
ord-6a9cb6cd29ca43e8bdf09e19b3d1fb2c
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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