Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → Methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate

HRID 1276484Notes

Reaction equation

HRID 1276484 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])/[CH:2]=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO[CH2:15][N:16]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:17][Si](C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[C:23]1([CH2:22][N:16]2[CH2:17][CH:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:2]([C:1]([O:11][CH3:12])=[O:10])[CH2:15]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 6428458Methyl cinnamate, (Z)-

Product 1

HCID 11426434Methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylateYield 72.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.98 g (12.2 mmol) of methyl (Z)-cinnamate and 5.80 g (24.4 mmol) N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine in 30 mL of CH2Cl2 at 0° C. was treated with 20 drops of trifluoroacetic acid and stirred cold for 1 h. The reaction mixture was partitioned between 200 mL of ether and 100 mL of sat'd NaHCO3 and the layers were separated. The organic layer was washed with 100 mL of sat'd NaCl, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 150 g of silica gel using 20:1 v/v CH2Cl2/ether as the eluant afforded 2.61 g (72%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.83 (t, J=8.7, 1H), 3.09-3.19 (m, 6H), 3.16 (s, 3H), 3.46-3.51 (m, 1H), 3.73-3.79 (m, 3H), 7.19-7.42 (1OH). Mass Spectrum (NH3 -CI): m/z 296 (M+1).

Workup

  1. customThe reaction mixture was partitioned between 200 mL of ether and 100 mL of sat'd NaHCO3
  2. customthe layers were separated
  3. washThe organic layer was washed with 100 mL of sat'd NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e81ea7e5c66b42a9bd5616b9df86c696
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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