Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-amino-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinol-3-carboxylate

HRID 583836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583836
O=[C:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.C([NH2:28])C1C=CC=CC=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH2:28][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[C@@H:4]([CH2:5][C@@H:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 148779783-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate

Produkt 1

HCID 60023865Ethyl (3S, 4aR, 6S, 8aR) 6-amino-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinol-3-carboxylateAusbeute 174,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a room temperature solution of ethyl 6-oxo-2-methoxycarbonyl-decahydroisoquinoline-3-carboxylate (4 g, 14.1 mmol), benzylamine (1.71 g, 15.9 mmol), and acetic acid (1.27 g, 21.2 mmol) in 1,2-dichloroethane (20 ml), sodium triacetoxyborohydride (5 g, 23.3 mmol) was added. The mixture was stirred under an atmosphere of nitrogen for 15 hours at room temperature. The reaction was quenched by adding aqueous saturated sodium bicarbonate, and extracted with dichloromethane three times. The organic layer was dried over sodium sulfate and evaporated to give 7 g of the title compound. The crude material was used in next step without further purification.

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby adding aqueous saturated sodium bicarbonate
  3. extractionextracted with dichloromethane three times
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-61b9cc8beaa34d6a80fe2957f208dc63
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924294B2

Notizen zur Reaktion

Wird geladen…