Diisopropylethylamine → (S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503925
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][SH:5].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[C:59]([O:63][C:64]([N:66]1[CH2:70][CH2:69][C@@H:68]([C:71]2[CH:76]=[CH:75][C:74](Br)=[CH:73][CH:72]=2)[CH2:67]1)=[O:65])([CH3:62])([CH3:61])[CH3:60].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:59]([O:63][C:64]([N:66]1[CH2:70][CH2:69][C@@H:68]([C:71]2[CH:76]=[CH:75][C:74]([S:5][CH2:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[CH:73][CH:72]=2)[CH2:67]1)=[O:65])([CH3:62])([CH3:60])[CH3:61]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 2055212-(Trimethylsilyl)ethanethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59428435(S)-3-(4-bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86586342KHSO4 Na2SO4

Produkt 1

HCID 59428461(S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
97.5 °C

Versuchsvorschrift

2-(Trimethylsilyl)ethane thiol (0.33 mL, 2.1 mmol), Pd2(dba)3 (183.9 mg), Xantphos (231.4 mg) and DIPEA (0.296 mL) were added to a solution of (S)-3-(4-bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (528 mg, 1.618 mmol) in 1,4-dioxane (7 mL) under nitrogen atmosphere. The reaction mixture was heated at 95-100° C. for 20 hours. After cooling to room temperature, a solution of 10% KHSO4/Na2SO4 was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 94/6) to give 616 mg (quantitative yield) of (S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 94/6)

Quellen und Nachweise

ORD-Eintrag
ord-bd20e92e6b154111965b251020c83993
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776910B2

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