Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 1-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl ester

HRID 1366461Notes

Reaction equation

HRID 1366461 reaction equation
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.[C:17]([O:22][CH3:23])(=[O:21])/[CH:18]=[CH:19]/[CH3:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:20][C@@H:19]1[CH2:3][N:4]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:5][C@H:18]1[C:17]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 3

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 638132Methyl Crotonate

Product 1

HCID 65589731-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl esterYield 116.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.8 mL, 7 mmol) and methyl crotonate (0.62 mL, 5.8 mmol) in DCM (25 mL) at 0° C. was added dropwise a solution of trifluoroacetic acid (0.045 mL, 0.58 mmol) in DCM (1 mL). The reaction was allowed to warm to room temperature and was stirred for 3 h. Saturated sodium bicarbonate solution was added and the phases were separated. The aqueous phase was extracted twice with DCM and the combined organics were dried over sodium sulfate and concentrated in vacuo. This yielded crude methyl rac-(trans)-4-methyl-1-(phenylmethyl)-3-pyrrolidinecarboxylate (1.58 g) which was used without further purification. LCMS: (M+H)+: 234.3.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted twice with DCM
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31a2b7a0850f4f6aa45d2a7103344384
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…