Methanol → HCID 14043879, Verbindung

HRID 1274438

Reaktionsgleichung

Reaktionsgleichung von HRID 1274438
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:10](OC)(OC)([O:12]C)[CH3:11].[CH3:18]O>>[C:10]([N:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([O:5][CH3:18])=[O:4])(=[O:12])[CH3:11]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 15050Trimethyl orthoacetateHCID 439227Pipecolic acid, (-)-

Produkt 1

HCID 14043879HCID 14043879, VerbindungAusbeute 50 %

Versuchsvorschrift

(S)-pipecolic acid (1.0 g, 7.7 mmol) was treated with trimethyl orthoacetate (15 ml, 171 mmol, 22 eq. 15 vol) and methanol (5 ml, 5 vol). The mixture was stirred and heated for 48 h and then concentrated in vacuo. The residue was dissolved in dichloromethane (10 ml) and filtered through a silica gel plug to yield N-acetylpipecolic acid, methyl ester (730 mg, 50%) which was racemic by GC analysis and had a 1H nmr spectrum which compared favourably with authentic material.

Aufarbeitung

  1. temperatureheated for 48 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  4. filtrationfiltered through a silica gel plug

Quellen und Nachweise

ORD-Eintrag
ord-9c61bd7393a649b284eb83d7df347350
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156900

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