Trifluoroacetic acid → 1-Benzyl-3-morpholin-4-ylmethyl-pyrrolidine-3-carboxylic acid methyl ester

HRID 1038070Notes

Reaction equation

HRID 1038070 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[CH2:5].O([CH2:16][N:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:18][Si](C)(C)C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:4]1([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:5][CH2:16][N:17]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:18]1)=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 589464832-Morpholin-4-ylmethyl-acrylic acid methyl ester

Product 1

HCID 576863371-Benzyl-3-morpholin-4-ylmethyl-pyrrolidine-3-carboxylic acid methyl esterYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred cold solution (0° C.) of 2-morpholin-4-ylmethyl-acrylic acid methyl ester (110 mg, 0.594 mmols) and N-(methoxylmethyl)-N-(trimethylsilylmethyl)-benzylamine (182 μl, 0.71 mmols) in dichloromethane (2 ml) was added slowly trifluoroacetic acid (9 μl, 0.12 mmols). The resulting solution was allowed to stir at rt overnight and directly purified by column chromatography eluting with ethyl acetate to provide title compound as clear oil (86 mg, 45%).

Workup

  1. customdirectly purified by column chromatography
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3488847daa934b75b1c4beb99bf66a89
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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