Dichloromethane → HCID 131723268, compound

HRID 2186342Notes

Reaction equation

HRID 2186342 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][CH:27]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9][C@@H:8]1[C:22]([O:24][CH3:25])=[O:23].ClCCl>CO.O>[OH:3][CH:4]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][CH:27]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9][C@@H:8]1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 131723269HCID 131723269, compound

Product 1

HCID 131723268HCID 131723268, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

0.15 g of sodium borohydride was added portionwise at a temperature in the region of 20° C. and under an inert atmosphere to a stirred solution of 1.59 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-3-carboxylate in 25 cm3 of methanol. The mixture was subsequently stirred for 75 minutes at a temperature in the region of 20° C. 15 cm3 of distilled water were then added while maintaining the same temperature. The mixture, with a milky appearance, was concentrated under reduced pressure (5 kPa) at a temperature in the region of 30° C. The residue obtained was taken up in 40 cm3 of distilled water to which have been added 80 cm3 of dichloromethane, stirred, and then separated by settling. The organic phase was withdrawn and then washed with one times 40 cm of water and dried over magnesium sulfate. After filtering through paper and then evaporating the solvent under reduced pressure (5 kPa) at a temperature in the region. of 40° C., 1.39 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-3-carboxylate were obtained in the form of a sticky solid with a foamy appearance and an orange color.

Workup

  1. temperaturewhile maintaining the same temperature
  2. concentrationThe mixture, with a milky appearance, was concentrated under reduced pressure (5 kPa) at a temperature in the region of 30° C
  3. customThe residue obtained
  4. stirringstirred
  5. customseparated
  6. customThe organic phase was withdrawn
  7. washwashed with one times 40 cm of water
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtering through paper
  10. customevaporating the solvent under reduced pressure (5 kPa) at a temperature in the region

Sources & evidence

ORD record
ord-66f0123f87d74d06ae15023132b628ce
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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