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Hydrochloric Acid → (R)-ethyl 2-(pyrrolidin-3-yloxy)acetate hydrochloride

HRID 2424925
Notes
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Reaction equation

HRID 2424925 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C@@H:8]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)=[O:5])[CH3:2].[ClH:20]>O1CCOCC1>[ClH:20].[NH:10]1[CH2:11][CH2:12][C@@H:8]([O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67234137tert-Butyl (3R)-3-(ethoxycarbonylmethoxy)pyrrolidine-1-carboxylate

Product 1

HCID 86624329(R)-ethyl 2-(pyrrolidin-3-yloxy)acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (3R)-3-(ethoxycarbonylmethoxy)pyrrolidine-1-carboxylate (4.0 g, 15.42 mmol) was dissolved in 4N HCl in 1,4-dioxane (50 mL), stirred at ambient temperature for 3 hrs, evaporated, co-evaporated with 1,4-dioxane (3×50 mL) and dried under high vacuum to give (R)-ethyl 2-(pyrrolidin-3-yloxy)acetate hydrochloride as an orange oil that solidified on standing. (3.2 g, 100%).

Workup

  1. customevaporated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-c8e5e354f8604ad49ced33df415a0edf
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07964618B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes