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

HRID 1917281Notes

Reaction equation

HRID 1917281 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+]>C(Cl)Cl>[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 86664645(E)-(R)-5-(tert-Butyldimethylsilyloxy)-4-methylpent-2-ene

Product 1

HCID 674907991-Benzyl-4-[(R)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (16.6 mL, 65.0 mmol) was added to a solution of (E)-(R)-5-(tert-butyldimethylsilyloxy)-4-methylpent-2-ene acid methyl ester (14 g, 54.2 mmol) in methylene chloride (100 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 14.6 g (69%) 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-5cf4918330174b1286454efde22d1e20
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…