Hydrochloric Acid → (4R)-4-Hydroxy-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl]pyrrolidine hydrochloride
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][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=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][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=2)[CH2:11]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 348 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-{2-[2-(3-methylphenyl)ethyl]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 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, the resulting solid residue was dissolved in methylene chloride, and ethyl acetate was added to the solution, which was then allowed to stand at room temperature. The crystals which precipitated were collected by filtration and dried in vacuo, to give 208 mg (yield 70%) of the title compound as colorless crystals, melting at 141°-143° C.
Workup
- customAt the end of this time, the solvent was removed by distillation under reduced pressure
- dissolutionthe resulting solid residue was dissolved in methylene chloride
- additionethyl acetate was added to the solution, which
- customto stand at room temperature
- customThe crystals which precipitated
- filtrationwere collected by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-6c3b776c5d534572b954cd3532ff17b4
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556864
Reaction notes
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