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

HRID 335059

Reaktionsgleichung

Reaktionsgleichung von HRID 335059
[NH2:1][C@H](C(O)=O)C.C([O-])=O.[Na+].OP([O-])([O-])=O.[Na+].[Na+].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.[CH2:78]([O:85][C@@H:86]1[C:91](=O)[CH2:90][CH2:89][O:88][CH2:87]1)[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH2:78]([O:85][C@@H:86]1[C@@H:91]([NH2:1])[CH2:90][CH2:89][O:88][CH2:87]1)[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1

Komponenten

11

Edukt 8

HCID 313Hydrochloric AcidHCID 1051Pyridoxal 5'-phosphateHCID 5950L-AlanineHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 439153NadhHCID 2723810Sodium FormateHCID 60209906(3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one

Produkt 1

HCID 60209907(3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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 P1G5 (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 hours, 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.

Aufarbeitung

  1. dissolutionAfter all the components were completely dissolved
  2. customaged at 30° C
  3. filtrationThe mixture was filtered through a bed of Solka Floc
  4. washthe cake was washed with ethyl acetate (250 mL)
  5. customThe combined filtrates were separated
  6. extractionthe aqueous layer was extracted a second time with ethyl acetate (2 L)
  7. concentrationThe combined organic extracts were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5c9ce06e2cd94dbda2c5e9df979ade6f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883850B2

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