Trifluoroacetic acid → 1-Benzyl-4-[(S)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl ester

HRID 1917290Notes

Reaction equation

HRID 1917290 reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17]([O:24][CH2:25][C@@H:26]([CH3:30])/[CH:27]=[CH:28]/[CH3:29])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].FC(F)(F)[C:33](O)=[O:34].O.C(=O)(O)[O-:40].[Na+]>ClCCl>[CH3:33][O:34][C:29]([CH:28]1[CH:27]([C@H:26]([CH3:30])[CH2:25][O:24][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1)=[O:40]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 86585896Sodium bicarbonate waterHCID 86664646HCID 86664646, compound

Product 1

HCID 674907801-Benzyl-4-[(S)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (2.97 mL, 11.6 mmol) was added to a solution of (E)-(S)-5-(tert-butyldimethylsilyloxy)-4-methylpent-2-ene acid methyl ester (2.5 g, 9.67 mmol) in dichloromethane (20 mL), and then a trace amount of trifluoroacetic acid was added. The mixture was stirred for 30 minutes and then saturated sodium bicarbonate water was added. The organic layer was separated and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 3.0 g (78%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d2c146ee24344d8a8f7ef0d28816a10a
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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