반응 #169649

반응 방정식

NAD

Potassium carbonate

4,4-dimethoxydihydro-2H-pyran-3(4H)-one

NaOH

potassium dihydrogenphosphate

sodium formate

L-Alanine

→

(3S)-4,4-dimethoxytetrahydro-2H-pyran-3-amine

용매

toluene

toluene

acetonitrile

반응 조건

후처리

1. 1
   추출extracted 3× with water (270 mL)
2. 2
   workup.ADDITIONwere added
3. 3
   온도cooled to rt
4. 4
   workup.WAITAfter 30 min
5. 5
   여과the reaction was filtered through a pad of solka-floc
6. 6
   기타The filtrate was partitioned
7. 7
   추출the aqueous layer was extracted with additional acetonitrile (810 mL)
8. 8
   농축The combined organic fractions were concentrated in vacuo

실험 절차

A solution of 4,4-dimethoxydihydro-2H-pyran-3(4H)-one (172 g, 1.07 mol, see Example 1) in 310 mL of toluene was stirred in toluene for 30 min, then extracted 3× with water (270 mL). To the aqueous solution was added potassium dihydrogenphosphate (14.1 g, 0.104 mol), sodium formate (55.1 g, 0.810 mol), and L-Alanine (72.2 g, 0.810 mol). The pH was adjusted to 7.8 with 5N NaOH, and NAD (0.810 g), PLP (0.810 g), LDH (0.162 g), FDH (1.62 g), and Codexis TA P1 G5 (4.05 g) were added. The mixture was heated to 45° C. for 12 h, then cooled to rt. Potassium carbonate (324 g, 2.34 mol) was added, and after 30 min, the mixture was diluted with acetonitrile (810 mL). After 30 min, the reaction was filtered through a pad of solka-floc. The filtrate was partitioned and the aqueous layer was extracted with additional acetonitrile (810 mL). The combined organic fractions were concentrated in vacuo to provide crude (3S)-4,4-dimethoxytetrahydro-2H-pyran-3-amine.

출처