Hydrochloric Acid → (S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine

HRID 743282Notes

Reaction equation

HRID 743282 reaction equation
Cl.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]=[C:26]([O:30][CH3:31])[CH:25]=1)=O)(C)(C)C>O1CCOCC1>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([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:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53745428(S)-1-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}pyrrolidine

Product 1

HCID 53750852(S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}pyrrolidineYield 73%

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 1.65 g of (S)-1-t-butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]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 2.5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting oily residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 910 mg (yield 73%) of the title compound as a colorless oil.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe resulting oily residue was purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-c2ce19f38b9f473385c1f42fbefb86a9
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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