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Preparation of VH Intermediates (3aS,6aR)-1,3-dibenzyl-hexahydro-1H-Furo "3,4-d" Imidazole-2,4-dione

Author: ChenChaoTian
Tutor: HanWei；YeWeiDong
School: East China University of Science and Technology
Course: Chemical Engineering
Keywords: VH intermediates imide sodium borohydride selective reduction
CLC: TQ252.3
Type: Master's thesis
Year: 2011
Downloads: 17
Quote: 0
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Abstract


The preparation method of (3aS,6aR)-1,3-dibenzyl-hexahydro-1H-furo [3,4-d] imidazole-2,4-dione that is a important intermediate of VH was studied in the paper. The precise chiral structure of (3aS,6aR)-1,3-dibenzyl-hexahydro-1H-furo [3,4-d] imidazole-2,4-dione was determined by single-crystal X-ray diffraction structure determination, and its NMR spectrum was resolved by combining with the crystal structure.In the first, the measure method about the area selectivity of sodium borohydride reduction was set up. The products were restored by sodium borohydride, and then were hydrolyzed to lactones. The specific rotations of lactones were measured. According to the formula: X%=100×([α]D20+60)/120The optical purity of the target products could be calculated by the formula. Which area was selected preferentially in the sodium borohydride reduction when in kinds of conditions could be judged by the method.The acid synthesis was synthesized to imide in the original technology condition, then restored and hydrolyzed to lactones. The optical rotations of lactones were measured. The area selectivity of the reduction which imide was restored by sodium borohydride could be judged with the results. The area selected ratio of sodium borohydride restoring imide 6 and 4 carbonyl was 9.9:1.Finally, the imides were modified by 1’-hydroxy single acetylation and 1’and 2’hydroxyl modification of diacetyl, then restored and hydrolyzed to lactones. The data of their optical ratations indicated in the process of the imide modified by 1’hydroxyl single acetylation, the area selectivity of the sodium borohydride reduction increased to 35.4:1. But the result of 1’ and 2’hydroxyl modification of diacetyl reduced to 2.3:1. A new way for further technology research was provided by the conclusion.

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of heterocyclic compounds > Containing five pairs or more different atoms of heterocyclic > Between the two nitrogen -mao ( imidazole) and its derivatives
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