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US 8,865,893 B2Granted
Method for preparing 2-morpholinoisobornane-10-thiol and intermediates formed therein
AssigneeNational Tsing Hua University
InventorsBiing-Jiun Uang, Yu-Han Tsao, Ping-Yu Wu
Life of this patent
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Abstract
A method for preparing 2-morpholinoisobornane-10-thiol is disclosed, which has simplified steps and avoids the use of Na metal. Accordingly, it is advantageous to apply the method in a mass production.
Claims19
A method for preparing 2-morpholinoisobornane-10-thiol, comprising the following steps:
- (a) providing a compound represented by formula (I),
- wherein each of R1 and R2, independently, is C1-6 alkyl, C5-10 cycloalkyl, C4-9 heterocycloalkyl, C6-10 aryl, or C5-9 heteroaryl, and the heterocycloalkyl and the heteroaryl have at least one heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, or R1 and R2 together form —(CH2)xZ(CH2)y—, wherein x and y is 1, 2, or 3, and Z is CH2, NH, O, or S;
- (b) converting the compound represented by formula (I) into a compound represented by formula (II),
- (c) reducing the compound represented by formula (II) into a compound represented by formula (III),
- (d) forming a compound represented by formula (IV),
- by N-alkylation of the compound represented by formula (III) with W1—(CH2)2O(CH2)2—W2, wherein W1 and W2 are leaving groups;
- and
- (e) reducing the compound represented by formula (IV) into 2-morpholinoisobornane-10-thiol.
5 more elements
A method for preparing 2-morpholinoisobornane-10-thiol, comprising the following steps:
- (a) providing a compound represented by formula (IV),
- wherein each of R1 and R2, independently, is C1-6 alkyl, C5-10 cycloalkyl, C4-9 heterocycloalkyl, C6-10 aryl, or C5-9 heteroaryl, and the heterocycloalkyl and the heteroaryl have at least one heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, or R1 and R2 together form —(CH2)xZ(CH2)y—, wherein x and y is 1, 2, or 3, and Z is CH2, NH, O, or S;
- and
- (b) reducing the compound represented by formula (IV) into 2-morpholinoisobornane-10-thiol.
1 more element
A compound represented by formula (VI):
- wherein is a single bond, Ra is morpholino, and Rb is
- wherein each of R1 and R2, independently, is C1-6 alkyl, C5-10 cycloalkyl, C4-9 heterocycloalkyl, C6-10 aryl, or C5-9 heteroaryl, and the heterocycloalkyl and the heteroaryl have at least one heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, or R1 and R2 together form —(CH2)xZ(CH2)y—, wherein x and y is 1, 2, or 3, and Z is CH2, NH, O, or S.
Dependencies are inferred from the claim text.