Hydrochloric Acid → (+)-3-Phenyl-3-(2-hydroxyethyl)pyrrolidine hydrochloric acid salt

HRID 343521Notes

Reaction equation

HRID 343521 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=O)(C)(C)C.[ClH:22].O1CCOCC1>C(OCC)C>[ClH:22].[C:16]1([C:10]2([CH2:13][CH2:14][OH:15])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 18465021Tert-butyl 3-(2-hydroxyethyl)-3-phenylpyrrolidine-1-carboxylate

Product 1

HCID 18464563(+)-3-Phenyl-3-(2-hydroxyethyl)pyrrolidine hydrochloric acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Combine 1-t-butoxycarbonyl-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (13.0 g, 44.6 mmol) and a solution of hydrochloric acid in dioxane (22.3 mL, 4M, 89.2 mmol). Heat to 50° C. After 1 hour, cool and add diethyl ether to give a solid. Collect the solid by filtration to give, after drying, the title compound: mp; 161°-163° C. [α]2D0 =+11.8 (c=0.563, methanol). Elemental Analysis calculated for C12H17NO·HCl: C 63.29; H 7.97; N 6.15; Found: C 63.21; H 7.86; N 6.05.

Workup

  1. temperaturecool
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-d47becafdd4f4ae684e3cc5d9d2599c9
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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