Process for Production of Optically Active Fluoroamine
AssigneeCentral Glass Company, Limited
InventorsAkihiro Ishii, Takako Yamazaki, Manabu Yasumoto
Life of this patent
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Abstract
Disclosed is a process for producing a protected optically active fluoroamine, which comprises the step of reacting an imine-protected optically active hydroxyamine, an oxazolidine-protected optically active hydroxyamine, or a mixture of the imine-protected optically active hydroxyamine and the oxazolidine-protected optically active hydroxyamine, with sulfuryl fluoride (SO2F2) in the presence of a tertiary amine having a carbon number of 7 to 18 (produced by substituting all of three hydrogen atoms in ammonia by alkyl groups). The desired optically active fluoroamine can be produced by hydrolyzing the protected optically active fluoroamine under acidic conditions.
Claims11
A process for producing a protected optically active fluoroamine of the formula [3], comprising:
- reacting an imine-protected optically active hydroxyamine of the formula [1], an oxazolidine-protected optically active hydroxyamine of the formula [2] or a mixture thereof with sulfuryl fluoride (SO2F2) in the presence of a tertiary amine in which all of three ammonia hydrogen atoms have been replaced by alkyl groups and which has a carbon number of 7 to 18
- where R1 and R2 each independently represent an alkyl group or an aromatic ring group;
- * represents an asymmetric carbon;
- the stereochemistry of the asymmetric carbon is maintained through the reacting;
- and the wavy line indicates in the formula (1) and in the formula (3) that the nitrogen-carbon group is in an E-configuration, a Z-configuration or a mixture thereof and indicates in the formula (2) that the substituent group R1 is in a syn-configuration, an anti-configuration or a mixture thereof.
A protected optically active fluoroamine of the formula [3]
- where R1 and R2 each independently represent an alkyl group or an aromatic ring group;
- * represents an asymmetric carbon;
- and the wavy line indicates that the nitrogen-carbon double bond is in an E-configuration, a Z-configuration or a mixture thereof.
Dependencies are inferred from the claim text.