Methanol → HCID 131724015, compound

HRID 394717Notes

Reaction equation

HRID 394717 reaction equation
[OH:1][CH:2]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][C:22]=1[F:33])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH:6]1[C:18]([OH:20])=[O:19].S(Cl)([Cl:36])=O.[CH3:38]O>>[ClH:36].[ClH:36].[OH:1][CH:2]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][C:22]=1[F:33])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH:6]1[C:18]([O:20][CH3:38])=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 22643927HCID 22643927, compound

Product 1

HCID 131724015HCID 131724015, compound

Procedure

A solution of 1.26 g of (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-carboxylic acid in 50-cm3 of methanol was cooled to a temperature in the region of −25° C. with stirring and under an inert atmosphere. 1.6-cm3 of thionyl chloride were added to this solution over 25 minutes. The mixture was brought to a temperature in the region of 20° C., while the stirring was continued for a further 48 hours. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C., taken up in 100-cm3 of toluene and the mixture was again concentrated under reduced pressure (5 kPa). The residue was taken up in 50-cm3 of diisopropyl ether, triturated and concentrated to dryness under reduced pressure (5 kPa). 1.17 g of methyl (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate dihydrochloride were obtained in the form of a yellow powder.

Workup

  1. customwas brought to a temperature in the region of 20° C., while the stirring
  2. concentrationThe reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  3. concentrationthe mixture was again concentrated under reduced pressure (5 kPa)
  4. customtriturated
  5. concentrationconcentrated to dryness under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-fd4802407d624225a3dd670e5acf3898
Source dataset
uspto-grants-2003_08
Patent number
US06602884B2

Reaction notes

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