Hydrochloric Acid → (4R)-4-Hydroxy-2-[2-(2-phenylethyl)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]=[CH:27][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]=[CH:27][CH:26]=2)[CH2:11]1Participants
Procedure
3 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 200 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in step (b) above] in 3 ml of dioxane, and the resulting solution was stirred at room temperature for 2 hours. At the end of this time, the solution was concentrated by distillation under reduced pressure, the resulting residue was dissolved in a small amount of methylene chloride, and ethyl acetate was added to the solution. The resulting mixture was then allowed to stand an room temperature. The crystals which precipitated were collected by filtration, to give 133 mg (yield 79%) of the title compound as colorless crystals, melting at 143°-145° C.
Workup
- concentrationAt the end of this time, the solution was concentrated by distillation under reduced pressure
- dissolutionthe resulting residue was dissolved in a small amount of methylene chloride, and ethyl acetate
- additionwas added to the solution
- customto stand an room temperature
- customThe crystals which precipitated
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-67c6b4dc97a8403aa0f84eedd6fef66c
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556864
Reaction notes
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