Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-(2-ethoxycarbonyl-4-fluoro-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

HRID 583841Notes

Reaction equation

HRID 583841 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.[CH2:21]([O:23][C:24](=[O:33])[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[NH2:32])[CH3:22].C(O)(=O)C.[Na]>CCCCCC.C(OCC)(=O)C>[CH2:21]([O:23][C:24]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[NH:32][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:33])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 11126923Ethyl 2-amino-5-fluorobenzoateHCID 148779783-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 131725055Ethyl (3S, 4aR, 6S, 8aR) 6-(2-ethoxycarbonyl-4-fluoro-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following the procedures from Example 1A, and using ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (537 mg, 1.9 mmol), 2-amino-5-fluoro-benzoic acid ethyl ester (183 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 95 mg (22% yield) of the title compound.

Sources & evidence

ORD record
ord-8ea732db089447bc8de90f2077c07d8b
Source dataset
uspto-grants-2005_08
Patent number
US06924294B2

Reaction notes

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