Methanol → Methyl 1-amino-4,4-difluorocyclohexanecarboxylate hydrochloride
Reaction equation
[NH2:1][C:2]1([C:10]([OH:12])=[O:11])[CH2:7][CH2:6][C:5]([F:9])([F:8])[CH2:4][CH2:3]1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[NH2:1][C:2]1([C:10]([O:12][CH3:17])=[O:11])[CH2:7][CH2:6][C:5]([F:9])([F:8])[CH2:4][CH2:3]1Participants
4
Conditions
- Temperature
- 70 °C
Procedure
Under argon, 4.30 g of the compound from Example 3A were initially charged in 100 ml of methanol at 0 to 5° C. 10 ml of thionyl chloride were added dropwise, and the mixture was stirred at 0° C. for 30 minutes and at 70° C. for 24 h. The mixture was then cooled to 5° C. and the precipitate was filtered off with suction. The solution was concentrated using a rotary evaporator and the residue was crystallized using methyl tert-butyl ether. This gave 5.20 g (quantitative, still contains salts) of the title compound.
Workup
- temperatureThe mixture was then cooled to 5° C.
- filtrationthe precipitate was filtered off with suction
- concentrationThe solution was concentrated
- customa rotary evaporator
- customthe residue was crystallized
Sources & evidence
- ORD record
- ord-71dd19b43fab4d769598e49585922ce2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946124B2
Reaction notes
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