Trifluoroacetic acid → (trans)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2405760Notes

Reaction equation

HRID 2405760 reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:29])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1.[C:30](O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH2:17]([O:18][C:19]([C@H:20]1[C@H:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1)=[O:29])[CH3:30]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 53143142-Propenoic acid, 3-(4-chlorophenyl)-, methyl ester, (2E)-

Product 1

HCID 12922292(trans)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl esterYield 255.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (2.05 mL, 8.0 mmol) and (E)-3-(4-chloro-phenyl)-acrylic acid methyl ester (1.57 g, 8.0 mmol) in dichloromethane (16 mL) was added TFA (275 mg, 2.4 mmol). The mixture was stirred at 23° C. for 30 min then treated with saturated aqueous NaHCO3 (20 mL), extracted with dichloromethane (2×50 mL), dried with MgSO4, filtered, and concentrated. Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc) gave (trans)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.11 g, 80%).

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-0f1a08ce35f8417dbe082d0ee53cf928
Source dataset
uspto-grants-2014_08
Patent number
US08809326B2

Reaction notes

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