Carbon tetrabromide → 3-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 42135

Reaktionsgleichung

Reaktionsgleichung von HRID 42135
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([Br:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinol

Produkt 1

HCID 426142173-Bromo-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (RS) 1-tert-butoxycarbonyl-3-pyrrolidinol (Prepn. 3) (3.00 g) in THF (90 mL), triphenylphosphine (12.4 g) was added, then a solution of CBr4 (15.7 g) in THF (90 mL) was dropped and the mixture stirred overnight at room temperature. The organic solvent was evaporated and the residue was extracted with EtOAc (4×50 mL). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 80/20) to give (RS) 1-tert-butoxycarbonyl-3-bromopyrrolidine in 80% yield as yellow oil. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.85 (1H, m), 3.70-3.59 (1H, m), 3.55-2.10 (5H, m), 1.35 (9H, s).

Aufarbeitung

  1. customThe organic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc (4×50 mL)
  3. washThe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-35f8915470a1418a81cdc37cf87deb5f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536160B2

Verknüpfte Notizen

Wird geladen…