4-Hydroxypyrrolidine → 1-(Cyclopropylmethyl)pyrrolidin-3-ol

HRID 353954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353954
[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:21]1[CH:23]([CH:24](O)C#N)[CH2:22]1>CC(O)=O.C1COCC1.[OH-].[Na+]>[CH:23]1([CH2:24][N:4]2[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]2)[CH2:21][CH2:22]1

Komponenten

7

Edukt 3

HCID 982104-HydroxypyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrile

Produkt 1

HCID 219142731-(Cyclopropylmethyl)pyrrolidin-3-olAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Hydroxy-pyrrolidine (5.65 g, 65 mmol, 1.0 equiv) was dissolved in 100 mL of 1% AcOH in THF and cooled to 0° C. Na(OAc)3BH (24 g, 114 mmol, 1.75 equiv) and cyclopropylcarboxaldehyde (5.0 g, 71 mmol, 1.1 equiv) were added and the resulting mixture was stirred at 0° C. for 1 h and room temperature overnight (16 h). The reaction was diluted with 200 mL of 2 N NaOH, and the product was extracted 3×200 mL of CH2Cl2. The organic extracts were combined, dried over Na2SO4, decanted and concentrated to yield the desired product as a free-flowing oil (7.26 g, 79%) which was used without further purification; MS, m/z 142=M+1.

Aufarbeitung

  1. extractionthe product was extracted 3×200 mL of CH2Cl2
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cfec38c52dcc4f488f849b9814fb202c
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756372B2

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