Réaction #169621

Équation de réaction

L-Alanine

NAD

pyridoxal-5-phosphate

sodium phosphate dibasic

(3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one

HCl

sodium formate

potassium carbonate

→

(3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine

Solvants

ethyl acetate

water

Conditions de réaction

Traitement

1. 1
   workup.DISSOLUTIONAfter all the components were completely dissolved
2. 2
   Autreaged at 30° C
3. 3
   FiltrationThe mixture was filtered through a bed of Solka Floc
4. 4
   Lavagethe cake was washed with ethyl acetate (250 mL)
5. 5
   AutreThe combined filtrates were separated
6. 6
   Extractionthe aqueous layer was extracted a second time with ethyl acetate (2 L)
7. 7
   ConcentrationThe combined organic extracts were concentrated in vacuo

Mode opératoire

To a solution of L-Alanine (200 g, 2.24 mol), sodium formate (76.0 g, 1.12 mmol), and sodium phosphate dibasic (28.7 g, 202 mmol) in 2.25 L of water adjusted to pH 7.5 was added NAD (2.2 g, 3.21 mmol), pyridoxal-5-phosphate (2.2 g, 8.90 mmol), LDH (0.45 g, 0.22 mol), FDH (4.5 g, 0.20 mol), and TA P1 G5 (4.5 g, 0.22 mol). After all the components were completely dissolved, (3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one (45 g, 0.22 mol) was added and the pH was adjusted to pH 7.25 with 6 N HCl and aged at 30° C. After 15 h, potassium carbonate (700 g, 5.06 mol) was added slowly, followed by ethyl acetate (2.2 L). The mixture was filtered through a bed of Solka Floc and the cake was washed with ethyl acetate (250 mL). The combined filtrates were separated and the aqueous layer was extracted a second time with ethyl acetate (2 L). The combined organic extracts were concentrated in vacuo to provide crude (3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine.

Source