Trifluoroacetic acid → HCID 19067124, compound

HRID 481777Notes

Reaction equation

HRID 481777 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19](OC(C)(C)C)=[O:20])[CH:13]([CH3:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH:18]=[C:19]=[O:20])[CH:13]([CH3:26])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19067200HCID 19067200, compound

Product 1

HCID 19067124HCID 19067124, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.59 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-3-methylpiperidine was dissolved in 20 ml of methylene chloride, and 5 ml of trifluoroacetic acid was added to the solution. The solution was stirred overnight at room temperature, and the resulting solution was concentrated under reduced pressure to obtain N-benzyloxycarbonyl-4-carbonylmethyloxy-3-methylpiperidine, which was an oily product with no color. The concentrate was dissolved in 40 ml of DMF, and 1.93 g of BOP reagent, 1.09 g of 7-amino-2-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline obtained in Example 2, and 1.33 g of triethylamine were added to this solution in an ice bath. The solution was stirred overnight at room temperature, and the resulting solution was extracted with ethyl acetate, washed with water, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, and from the fractions eluted with chloroform-methanol (100:3 v/v) was obtained 1.14 g of 7-[1-(benzyloxycarbonyl)-2-methylpiperidine-4-yloxyacetylamino]-2-[2-(ethoxycarbonyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 49%).

Workup

  1. concentrationthe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7511a9350b14a37a381e7fdd4bb9555
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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