Tetrahydrofuran → tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 72416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72416
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O1CCCC1>C([O-])(O)=O.[Na+]>[OH:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Produkt 1

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 109,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To an ice cooled solution of 1-Boc-pyrrolidine-3-carboxylic acid (1 g, 4.64 mmol) in dry tetrahydrofuran (6 ml) Borane-methyl sulfide complex (2M in tetrahydrofuran) (3.48 ml, 6.96 mmol) was added dropwise the under N2 atmosphere The reaction mixture was stirred overnight at room temperature. NaHCO3 sat. sol. (20 ml) was added and the resulting mixture was stirred for 30 min. The mixture was extracted with ethylacetate (3×20 ml). Collected organics after solvent evaporation afforded the title compound (D39) (1.02 g)

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 30 min
  2. extractionThe mixture was extracted with ethylacetate (3×20 ml)
  3. customCollected organics after solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a74b8cbbab8e45ecb1597c2d25e7c5e3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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