PATENT CLAIM ANALYSIS

Application Number: 15876464
Application Type: Utility
Filing Date: 2018-01
Publication Date: 2018-05
Patent Classification: ["556", "415000"]

Abstract:
The present teachings relate to a functionalized silyl cyanide and synthetic methods thereof. As an example, the method may include adding a raw material silane and a cyanide source MCN in an organic solvent to produce the functionalized silyl cyanide in the absence of catalyst or in the presence of a metal salt catalyst. The functionalized silyl cyanide may be used in the reactions that classic TMSCN participates in, to synthesize important intermediates (e.g., cyanohydrin, amino alcohols and α-amino nitrile compounds), with improved reactivity and selectivity. The cyanosilyl ether resulted from the nucleophilic addition of functionalized silyl cyanide to aldehyde or ketone may undergo intramolecular reaction under appropriate conditions to transfer the functional groups on silicon onto the other parts of the product linked to silicon. Such a functional group transfer process may increase the synthesis efficiency and atom economy, as well as afford products unobtainable using traditional TMSCN.

Claim (Index 5):
Use of a functionalized silyl cyanide for synthesizing alcohol compounds bearing substituted ketone moiety via tandem nucleophilic addition reaction/functional group transfer reaction, comprising the step of:\n nucleophilic addition reaction of functionalized silyl cyanide 1aa with a carbonyl compound 3a provides an intermediate 4a which undergoes an intramolecular nucleophilic addition reaction promoted by base I and a hydrolysis reaction promoted by acid I; thereby producing alcohol compounds 5 bearing substituted ketone moiety; wherein, the tandem nucleophilic addition reaction/functional group transfer reaction comprises racemic tandem nucleophilic addition reaction/functional group transfer reaction and asymmetric tandem nucleophilic addition reaction/functional group transfer reaction; the alcohol compounds 5 are in R and/or S configuration; the reaction process is as shown in Scheme (III): wherein, Z is Cl, Br; R 2  is selected from C1-C20 alkyl, phenyl, C6-C20 substituted phenyl, naphthyl, C10-C20 substituted naphthyl, furanyl, C4-C10 substituted furanyl, thienyl, C4-C10 substituted thienyl, pyrryl, C4-C10 substituted pyrryl, pyridyl, and C5-C10 substituted pyridyl; R 3  is selected from H; C1-C20 alkyl; ester group CO 2 R, wherein, R=Me, Et, i-Pr, t-Bu, Ph, Bn; and amide CONR 2 , wherein, R=Me, Et, CF 3 ; the catalyst I is used for catalyzing the tandem nucleophilic addition reaction/functional group transfer reaction between the functionalized silyl cyanide 1aa and the carbonyl compound 3a; for the racemic tandem nucleophilic addition reaction/functional group transfer reaction, the catalyst is the catalyst I\u2032 as recited in  claim 3 ; and the dosage of the catalyst is 0.001-0.5 equivalent relative to the carbonyl compound 3a; for the asymmetric tandem nucleophilic addition reaction/functional group transfer reaction, the catalyst is the catalyst I\u2033 as recited in  claim 3 ; and the dosage of the catalyst is 0.001-0.5 equivalent relative to the carbonyl compound 3a; the base I is a strong base for removing hydrogen adjacent to FG; the acid I is an acidic catalyst used for hydrolyzing C\u2014Si and C\u2550N bond, which is selected from hydrochloric acid, sulfuric acid, acetic acid.

Metadata:
- Claim Count in Document: 15.0
- Percentile: 86.0
- Lexical Diversity: 1.60396
- Patent Class: 556.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['14547641', '14547696', '15102968', '15746646', '14609612']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.683282887384385
- 35 USC 102 Novelty (BERT): 0.5050706841111602
- Combined Prediction Score: 0.6654616670570626
- Mean Citation Score: 257.21133999999995
- Max Citation Score: 276.37405
- Similarity Product: 217.42014039979577

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test