Reaktion #40466

Reaktionsgleichung

sodium cyanoborohydride

L-serine-benzyl ester-HCl

benzaldehyde

sodium acetate

→

desired compound

Ausbeute 81.0%

N-benzyl-serine Benzyl Ester

Ausbeute 81.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned into ether and aqueous saturated sodium bicarbonate
2. 2
   ExtraktionThe separated organic phase was extracted with 1M HCl (3×)
3. 3
   WaschenCombined aqueous extracts were washed with ether
4. 4
   Extraktionextracted with ether
5. 5
   WaschenCombined organic extracts were washed with brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenconcentrated to dryness

Vorschrift

To a mixture of L-serine-benzyl ester-HCl (2.3 g), benzaldehyde(1.05 eq.) and sodium acetate (1 eq.) in methanol was added sodium cyanoborohydride (1.0 eq.). The resulting mixture was stirred at ambient temperature for 15 hrs, then partitioned into ether and aqueous saturated sodium bicarbonate. The separated organic phase was extracted with 1M HCl (3×). Combined aqueous extracts were washed with ether, basified with aqueous 4.5M K2CO3 and extracted with ether. Combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to dryness to give 2.32 g of the desired compound (waxy solid, 81% yield).

Quelle