Sodium Hydroxide → 3-Cyano-3-(pyrrolidin-1-YL)oxetane

HRID 560188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560188
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:6]1[CH2:9][C:8](=O)[CH2:7]1.C[Si]([C:15]#[N:16])(C)C.[OH-].[Na+]>ClCCl.C(O)(=O)C>[N:1]1([C:8]2([C:15]#[N:16])[CH2:9][O:6][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 82115Trimethylsilyl cyanideHCID 150242543-Oxetanone

Produkt 1

HCID 591979193-Cyano-3-(pyrrolidin-1-YL)oxetane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyrrolidine (7.4 g, 104 mmol) was slowly added at 0° C. to acetic acid (33 mL). 3-Oxetanone (1.5 g, 21 mmol) and trimethylsilyl cyanide (5.3 g, 52 mmol) were also added at 0° C. The reaction mixture was stirred at room temperature overnight and diluted with 100 mL dichloromethane. 32% sodium hydroxide solution was pH-9 (˜50 mL). The mixture was extracted twice with dichloromethane. The combined organic phases were dried on sodium sulfate, filtered and carefully evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol 1:0→19:1) yielded 3-pyrrolidin-1-yl-oxetane-3-carbonitrile as a light yellow oil (3.22 g, contains 19% dichloromethane, 92%), MS: m/e=153.1 [(M+H)+].

Aufarbeitung

  1. extractionThe mixture was extracted twice with dichloromethane
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customcarefully evaporated
  5. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol 1:0→19:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea137df4186c4fb3bbac16c29f9c0924
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063098B2

Notizen zur Reaktion

Wird geladen…