1,4-Dioxa-8-azaspiro(4.5)decane → 7-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxyquinoline

HRID 494969Notes

Reaction equation

HRID 494969 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH:14]=O)[N:9]=[CH:8][CH:7]=[CH:6]2.[O:16]1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[O:16]1[C:20]2([CH2:25][CH2:24][N:23]([CH2:14][CH2:13][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][CH:8]=[N:9]4)=[CH:4][C:3]=3[O:2][CH3:1])[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57682887(6-Methoxyquinolin-7-yl)acetaldehyde

Product 1

HCID 576827747-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxyquinolineYield 30.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

1.45 g of (6-methoxyquinolin-7-yl)acetaldehyde and 0.63 g of 1,4-dioxa-8-azaspiro[4.5]decane were dissolved in 20 ml of methylene chloride. Thereafter, 0.42 ml of acetic acid and 0.74 g of sodium triacetoxyborohydride were added to the reaction solution, and the obtained mixture was then stirred at room temperature for 3 hours. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol), so as to obtain 445 mg of the subject compound.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-39b4b269516a407ab031ca4aec07bf5f
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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