Trifluoroacetic acid → HCID 68089490, compound

HRID 1524284Notes

Reaction equation

HRID 1524284 reaction equation
[CH2:1]([N:8]([CH2:13]OC)[Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:28])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1.F[C:30](F)(F)C(O)=O>C(Cl)Cl.O>[CH3:16][O:17][C:18]([C@H:19]1[C@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=2)[CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:30]1)=[O:28]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1482751Methyl 3-bromocinnamate, predominantly transHCID 23062047Benzyl-methoxymethyl-trimethylsilanyl-amine

Product 1

HCID 68089490HCID 68089490, compoundYield 1,457.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add benzyl-methoxymethyl-trimethylsilanyl-amine (14.7 g, 2.20 mmol) to a solution of trans-3-(3-bromo-phenyl)-acrylic acid methyl ester (10.0 g, 41.4 mmol) in methylene chloride (80 mL). Cool the mixture to 0° C. and stir for 10 min then add trifluoroacetic acid (0.92 mL, 12.4 mmol) and stir the mixture at 0° C. for an additional 4 h. Dilute the reaction mixture with water and extract with methylene chloride. Dry the combined organic phase over anhydrous sodium sulfate and concentrate under reduced pressure. Purify the residue by silica gel chromatography to provide 12 g (77%) of trans-1-benzyl-4-(3-bromo-phenyl)-pyrrolidine-3-carboxylic acid methyl ester.

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry the combined organic phase over anhydrous sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-49028adc37f34e57a7004cc4f7a7b612
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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