Methanol → Methyl 1-acetylpiperidine-2-carboxylate
Reaktionsgleichung
[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
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.