Lithium Hydroxide → 1-(Cyanomethyl)-L-proline

HRID 1257638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257638
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]#[N:12])=[O:4].[OH-].[Li+]>C1COCC1>[C:11]([CH2:10][N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])#[N:12]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 30491532Methyl 1-(cyanomethyl)-L-prolinate

Produkt 1

HCID 341784361-(Cyanomethyl)-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (S)-1-cyanomethyl-pyrrolidine-2-carboxylic acid methyl ester (100 mg, 0.60 mmol) and lithium hydroxide (16 mg, 0.66 mmol) in THF (2 mL) was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under vacuum and the resulting residue dissolved in water (5 mL) and neutralized with 1M aqueous HCl. The resulting solution was freeze-dried to afford (S)-1-cyanomethyl-pyrrolidine-2-carboxylic acid. 1H NMR (300 MHz, CDCl3) δ: 3.80 (d, 2H), 3.53 (dd, 1H), 3.25 (m, 1H), 2.85 (m, 1H), 2.40-1.94 (m, 4H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe resulting residue dissolved in water (5 mL)
  3. customThe resulting solution was freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-caf791d9b9814345b34c688557aaf683
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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