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US 10,538,539 B2Granted
Method for preparing 3-((2S, 5S)-4-methylene-5-(3-oxopropyl)tetrahydrofurane-2-yl) propanol derivative, and intermediate therefor
AssigneeYonsung Fine Chemical Co., Ltd.
InventorsHyun Ik Shin, Kee Young Lee, Changyoung Oh
Life of this patent
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Abstract
A method for preparing a 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivative by a simple process with high yields, and an intermediate useful for the method.
Claims8
A process for preparing a 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivative of the following formula (1), which comprises the steps of:
- (i) reacting a compound of the following formula (4) with allyl bromide to obtain a compound of the following formula (5);
- (ii) reacting the compound of the following formula (5) with an arylsulfonyl azide to obtain a triazole compound of the following formula (6);
- (iii) subjecting the triazole compound of the following formula (6) to denitrification and rearrangement followed by hydrolysis to obtain a tetrahydrofuran compound of the following formula (7);
- (iv) subjecting the tetrahydrofuran compound of the following formula (7) to Wittig reaction to obtain a compound of the following formula (8);
- (v) subjecting the compound of the following formula (8) to hydroboration followed by oxidation to obtain a compound of the following formula (9);
- and
- (vi) oxidizing a hydroxyl group of the compound of the following formula (9):
- wherein,
- R is an arylsulfonyl group substituted or unsubstituted with C1-C6 alkyl group, and
- PG represents a protecting group.
7 more elements
A process for preparing a compound of the following formula (1), which comprises the steps of:
- (iii) subjecting a triazole compound of the following formula (6) to denitrification and rearrangement followed by hydrolysis to obtain a tetrahydrofuran compound of the following formula (7);
- (iv) subjecting the tetrahydrofuran compound of the following formula (7) to Wittig reaction to obtain a compound of the following formula (8);
- (v) subjecting the compound of the following formula (8) to hydroboration followed by oxidation to obtain a compound of the following formula (9);
- and
- (vi) oxidizing a hydroxyl group of the compound of the following formula (9):
- wherein,
- R is an arylsulfonyl group substituted or unsubstituted with C1-C6 alkyl group, and
- PG represents a protecting group.
5 more elements
Dependencies are inferred from the claim text.