Trifluoroacetic acid → HCID 58371944, compound

HRID 1020942Notes

Reaction equation

HRID 1020942 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C:4]([S:6][CH3:7])=[CH2:5].C(OC(=C)C(O)=O)C.[CH2:17]([N:24]([CH2:30]OC)[CH2:25][Si](C)(C)C)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:4]1([S:6][CH3:7])[CH2:5][CH2:25][N:24]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:30]1)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 86656202HCID 86656202, compound

Product 1

HCID 58371944HCID 58371944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-ethoxyacrylate 2-Methylsulfanyl-acrylic acid methyl ester 6BP (136 g, 1.03 mol) and benzyl-methoxymethyl-trimethylsilanylmethyl-amine 7BP (290 g, 1.22 mol) in dichloromethane (2.7 L ml) was added at 0° C. a solution of trifluoroacetic acid (26 mL, 0.3 mol). The resulting solution was warmed to room temperature and stirred for one overnight. The crude product was purified by column chromatography on silica gel eluting with a solution of ethyl acetate in hexane (1:4) to give 1-benzyl-3-methylsulfanyl-pyrrolidine-3-carboxylic acid methyl ester 8BP (131 g, 47%).

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solution of ethyl acetate in hexane (1:4)

Sources & evidence

ORD record
ord-3b5904df8e31460da28eef747ec30c0e
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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