Sodium Bicarbonate → HCID 19067180, compound

HRID 481785Notes

Reaction equation

HRID 481785 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([N+:23]([O-])=O)=[CH:18][CH:19]=2)[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:23][C:17]1[CH:16]=[C:15]2[C:20]([CH2:21][CH2:22][N:13]([CH2:12][CH2:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19067165HCID 19067165, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 19067180HCID 19067180, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.80 g of 2-(2-benzyloxycarbonylethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 10 ml of ethanol, and 4.77 g of tin chloride dihydrate was added to the solution. The solution was heated under reflux with stirring for 30 minutes. The resulting solution was neutralized by adding saturated aqueous solution of sodium bicarbonate, and the solution was extracted with ethyl acetate, washed with water and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the residue was purified by silica gel column chromatography to obtain 1.52 g of 7-amino-2-(2-benzyloxycarbonylethyl)-1,2,3,4-tetrahydroisoquinoline as an oily product. This product, with no further purification, was dissolved in 10 ml of DMF, and 1.52 g of 1-(tertbutoxycarbonyl)-4-(carboxymethoxy)piperidine and 0.41 g of 1-ethyl-3-(3-dimethylaminopopyl)carbodiimide, which had been separately synthesized, were added to this solution. The solution was stirred overnight at room temperature. 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 residue was purified by silica gel column chromatography to obtain 1.84 g of 2-(2-benzyloxycarbonylethyl)-7-[1-(tert-butoxycarbonyl)piperidine-4-yloxyacetylamino]-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 68%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. extractionthe solution was extracted with ethyl acetate
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous sodium sulfate
  6. customAfter separating the desiccant
  7. filtrationby filtration
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-720e2178579d4e5d86f97a7bc2d23a1d
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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