HCID 46831647, compound → 3-(Phenyl-o-tolyloxymethyl)pyrrolidine

HRID 1427720Notes

Reaction equation

HRID 1427720 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:9]1)=O)(C)(C)C>Cl.CCO>[C:22]1([CH:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 46831647HCID 46831647, compound

Product 1

HCID 446254813-(Phenyl-o-tolyloxymethyl)pyrrolidineYield 103.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-(Phenyl-o-tolyloxymethyl)pyrrolidine-1-carboxylic acid t-butyl ester (149 mg, 405 μmol) was dissolved in a solution of HCl in EtOH (1.25M, 3 mL) and stirred at room temperature for 3 hours, and then evaporated to dryness. The residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH:9/1) to afford the RS/SR mixture of enantiomers of the hydrochloride salt of the title compound as a yellow foam (112 mg, 98% purity).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH:9/1)
  3. customto afford

Sources & evidence

ORD record
ord-6b28d3eb049d4989b8bf0446179fc6ce
Source dataset
uspto-grants-2015_01
Patent number
US08933249B2

Reaction notes

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