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Sodium hydride → (2S)-4-Methylene-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1006859
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1006859
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:18]=1[CH2:19]Br.[H-].[Na+].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:19][C:18]1[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:17]=1[F:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27770572,4,5-Trifluorobenzyl BromideHCID 66733597tert-butyl (2S)-2-(hydroxymethyl)-4-methylidenepyrrolidine-1-carboxylate

Produkt 1

HCID 69427718(2S)-4-Methylene-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 9.6 g (45 mmol) (2S)-2-Hydroxymethyl-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester and 25 g (112.5 mmol, 2.5 eq) 2,4,5-trifluorobenzyl bromide in 950 ml THF were added 3.2 g (73.1 mmol, 50% in mineral oil, 1.6 eq) NaH at 0° C. over a period of 30 min. The reaction was warmed to RT over night, and added to a cooled mixture of saturated aqueous NH4Cl solution and EtOAc, the phases were separated and the inorganic one was extracted with EtOAc, the combined organic ones were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography using hexane/EtOAc 4:1 as an eluent yielding 5.4 g (34%) (2S)-4-Methylene-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as yellow oil, MS: 358 (MH+) and 1.7 g (13%) recovered starting material.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with EtOAc
  3. washthe combined organic ones were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bb870c6975e545509cfc0f26f33d7dc3
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06790860B2

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