Trifluoroacetic acid → 4-[3-(1-Aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]-1-methylpyrrolidin-2-one trifluoroacetate

HRID 511020Notes

Reaction equation

HRID 511020 reaction equation
[Cl:1][C:2]1[C:3]([CH3:27])=[C:4]([CH:20]2[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[CH2:21]2)[C:5]([O:18][CH3:19])=[C:6]([CH:8]([NH:10]C(=O)OC(C)(C)C)[CH3:9])[CH:7]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(Cl)Cl>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[NH2:10][CH:8]([C:6]1[C:5]([O:18][CH3:19])=[C:4]([CH:20]2[CH2:21][N:22]([CH3:26])[C:23](=[O:25])[CH2:24]2)[C:3]([CH3:27])=[C:2]([Cl:1])[CH:7]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666940Tert-butyl {1-[5-chloro-2-methoxy-4-methyl-3-(1-methyl-5-oxopyrrolidin-3-yl)phenyl]ethyl}carbamate

Product 1

HCID 866669414-[3-(1-Aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]-1-methylpyrrolidin-2-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solutions of the individual diastereoisomers of tert-butyl {1-[5-chloro-2-methoxy-4-methyl-3-(1-methyl-5-oxopyrrolidin-3-yl)phenyl]ethyl}carbamate (28 mg, 0.070 mmol [peak 1 from step 1]; 56 mg, 0.14 mmol [peak 2 from step 1]) in separate reaction flasks in methylene chloride (1 mL) were each treated individually with trifluoroacetic acid (1 mL) dropwise and stirred for 30 minutes. The reaction mixtures were individually concentrated to give diastereoisomer from peak 1 (38 mg, quantitative) and diastereoisomer from peak 2 (65 mg, quantitative) as residues that were used without further purification. Peak 1: LCMS for C15H19ClNO2 (M−NH2)+: m/z=280.1. Found: 280.1. Peak 2: LCMS for C15H22ClN2O2 (M+H)+: m/z=297.1. Found: 297.1.

Workup

  1. customThe reaction mixtures
  2. concentrationwere individually concentrated
  3. customto give diastereoisomer from peak 1 (38 mg, quantitative) and diastereoisomer from peak 2 (65 mg, quantitative) as residues that
  4. customwere used without further purification

Sources & evidence

ORD record
ord-344446ce08aa4ac09b8052663edfd17a
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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