Method for producing 5-hydroxypiperidine-2-carboxylic acid
A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R 3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R 3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).
1. A compound
represented by formula (6a) below:
wherein X represents Cl, Br, or I, P′ represents a tetrahydropyranyl group, methoxymethyl group, ethoxyethyl group, tert-butyl group, or tert-butyldimethylsilyl group, and R 3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms,
or a compound represented by formula (4a) below:
wherein X represents Cl, Br, or I, P′ represents a tetrahydropyranyl group, methoxymethyl group, ethoxyethyl group, or tert-butyldimethylsilyl group, and R 2 represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, or an aralkyl group containing 7 to 20 carbon atoms,
or a compound represented by formula (3a) below:
wherein X represents Cl, Br, or I, and P′ represents a tetrahydropyranyl group, methoxymethyl group, or ethoxyethyl group,
or a compound represented by formula (2a) below:
wherein X represents Cl, R 1 represents a hydrogen atom or an optionally substituted alkyl group containing 1 to 4 carbon atoms, P″ represents a tetrahydropyranyl group or ethoxyethyl group.
2. The compound according to claim 1 , wherein the compound represented by the formula (6a) is the compound selected from compounds represented by the formulae below:
(wherein Ac represents an acetyl group and Bz represents a benzoyl group).
3. The compound according to claim 1 , wherein the compound represented by the formula (4a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).
4. The compound according to claim 1 , wherein the compound represented by the formula (3a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).
5. The compound according to claim 1 , wherein the compound represented by the formula (2a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).
6. The compound (6a) according to claim 1 .
7. The compound (4a) according to claim 1 .
8. The compound (3a) according to claim 1 .
9. The compound (2a) according to claim 1 .
10. The compound according to claim 6 , wherein the compound represented by the formula (6a) is the compound selected from compounds represented by the formulae below:
(wherein Ac represents an acetyl group and Bz represents a benzoyl group).
11. The compound according to claim 7 , wherein the compound represented by the formula (4a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).
12. The compound according to claim 8 , wherein the compound represented by the formula (3a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).
13. The compound according to claim 9 , wherein the compound represented by the formula (2a) is the compound selected from compounds represented by the formulae below:
(wherein Et represents ethyl group).