Lithium borohydride → tert-Butyl (2R,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 732358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732358
[BH4-].[Li+].C[O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([F:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O>C1COCC1>[C:16]([O:15][C:13]([N:8]1[CH2:9][C@H:10]([F:12])[CH2:11][C@@H:7]1[CH2:5][OH:4])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 68687525(2R,4R)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 68815110tert-Butyl (2R,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add lithium borohydride (1.03 g, 47.4 mmol) to an ice cold solution of 4-(R)-fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 31.5 mmol) in THF (100 mL). Let warm to room temperature over 18 h. Cool in ice bath. Slowly add acetic acid (5 mL) and water and extract with ethyl acetate. Wash extract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a thick oil (5.56 g, 80%).

Aufarbeitung

  1. temperatureCool in ice bath
  2. extractionSlowly add acetic acid (5 mL) and water and extract with ethyl acetate
  3. washWash
  4. extractionextract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f86f6e7cf5fe4df39bb4b58e4ba3e370
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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