Acetic Acid → HCID 131725053, compound

HRID 583838Notes

Reaction equation

HRID 583838 reaction equation
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.[NH2:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([O-:26])=[O:25].[C:31](O)(=O)[CH3:32].[Na]>CCCCCC.C(OCC)(=O)C>[CH2:31]([O:25][C:24]([C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[NH:21][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)=[O:26])[CH3:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 54598422-aminobenzoateHCID 148779783-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 131725053HCID 131725053, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following the procedure from Example 3A, and using ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (537 mg, 1.9 mmol), 2-aminobenzoate (165 mg, 1.0 mmol), glacial acetic acid (0.36 mL, 6.0 mmol), and sodium triacethoxyborohydride (590 mg, 2.8 mmol), flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 181 mg (42% yield) of the title compound.

Sources & evidence

ORD record
ord-1134a1156ab2431680f65917927eb7df
Source dataset
uspto-grants-2005_08
Patent number
US06924294B2

Reaction notes

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