Methanol → HCID 86758158, compound

HRID 2186367Notes

Reaction equation

HRID 2186367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C@@H:17]1[CH2:29][C:30]([OH:32])=[O:31].S(=O)(=O)(O)O.[CH3:38]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]1[CH2:29][C:30]([O:32][CH3:38])=[O:31]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70173962HCID 70173962, compound

Product 1

HCID 86758158HCID 86758158, compound

Conditions

Temperature
20 °C

Procedure

A mixture of 2.8 g of (3R,4R)-4-(3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid in 100 cm3 of anhydrous methanol to which had been added 1 cm3 of 95% sulfuric acid was heated with stirring at a temperature in the region of the boiling point for 2 hours. After cooling to a temperature in the region of 20° C., the reaction mass was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then 20 cm3 of a saturated aqueous sodium hydrogencarbonate solution were added to the residue obtained. The mixture was extracted with 4 times 20 cm3 of dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.25 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-acetate were obtained in the form of an oil with a brown color.

Workup

  1. temperaturewas heated
  2. customthe reaction mass was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  3. addition20 cm3 of a saturated aqueous sodium hydrogencarbonate solution were added to the residue
  4. customobtained
  5. extractionThe mixture was extracted with 4 times 20 cm3 of dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-bd3677e54ca34dfcaa924fbddc536135
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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