1,2-Dichloroethane → Trifluoroacetic acid

HRID 2402857Notes

Reaction equation

HRID 2402857 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[C:8](=O)([O-])[NH2:9].Cl[CH2:13][CH2:14]Cl>>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[NH:9]1[CH2:8][CH2:14][CH2:13][CH2:1]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 276CarbamateHCID 6422Trifluoroacetic acid

Product 2

HCID 6422Trifluoroacetic acidHCID 31268Pyrrolidine

Procedure

TFA (250 μL, 3.24 mmol) was added to a solution of carbamate J5a in DCE (1 mL) and the reaction was stirred at rt for 1.5 hr. The reaction was concentrated under a stream of nitrogen to provide a TFA salt of pyrrolidine J5b (45 mg). LC-MS retention time 2.928 min; m/z 525.32 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10u C18 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. concentrationThe reaction was concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-0088cb604b314dbab75c74036034bfd5
Source dataset
uspto-grants-2014_08
Patent number
US08796466B2

Reaction notes

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