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Propellane derivates and synthesis

A technology of propane and alkyl, applied in the field of synthetic organic chemistry, which can solve the problems of reagent availability and cost constraints for commercial use

Active Publication Date: 2016-12-14
RECURIUM IP HLDG LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In short, the commercial use of BCP is limited by the availability and cost of reagents

Method used

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  • Propellane derivates and synthesis
  • Propellane derivates and synthesis
  • Propellane derivates and synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Example 1: General procedure

[0137] Prepare anhydrous EtOH, anhydrous MeOH, or anhydrous MeOH and anhydrous Et containing 1 ppm BHT (10 mM final concentration) 2 Fe(acac) in a ~2:1 mixture of O 3 solution (30 mol% or 50 mol%) and in N 2 under stirring for 2min. Add [1.1.1]propane (1 equiv, as dissolved in Et 2 O solution) and a suitable reagent (1.2-3 equiv.) capable of providing all or part of the substituents, followed by the addition of PhSiH 3 (1.0-1.5 equiv.). After stirring overnight at room temperature (RT), the mixture containing the product was concentrated to give the desired compound, which could be further purified by flash chromatography on silica gel, or the product was continued without isolation or purification to yield the corresponding derivative .

Embodiment 2

[0138] Example 2: Bicyclo[1.1.1]pentane-1-carbonitrile:

[0139]

[0140] Bicyclo[1.1.1]pentane-1-carbonitrile was prepared according to the general procedure using 4-methylbenzenesulfonyl cyanide (TsCN) as a suitable reagent capable of providing all or part of the substituents. 1 H NMR (400MHz, MeOH-d 4 ) δ 2.40 (s, 1H), 2.31 (s, 6H).

Embodiment 3

[0141] Example 3: Bicyclo[1.1.1]pentan-1-ylmethanamine

[0142]

[0143] By dissolving bicyclo[1.1.1]pentane-1-carbonitrile in anhydrous Et 2 Bicyclo[1.1.1]pentan-1-ylmethanamine was prepared by O (0.090M) and cooled to 0°C. A 2M solution of LAH in THF (5.3 equiv) was added dropwise with stirring. After 30 min, the solution was quenched at 0 °C by addition of EtOAc (2 mL). The mixture was concentrated to 30% of its original volume and loaded onto a Si-p-toluenesulfonic acid resin column. Rinse the column with MeOH followed by 1N NH in MeOH 3 The desired compound was eluted. The solution was concentrated to 10% of its original volume, then acidified with 4N HCl in dioxane, and concentrated to dryness to give bicyclo[1.1.1]pentan-1-ylmethanamine. 1 H NMR (400MHz, MeOH-d 4 )δ2.97(s,2H), 2.57(s,1H), 1.90(s,6H); LC / MS(APCI) m / z 98.1[C 6 H 11 N+H] + .

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Abstract

Disclosed herein are compounds of the general Formula (I), and methods of synthesizing substituted bicyclo[1.1.1 jpentanes. The synthetic methods described herein use a [1.1.1]propellane, a Group VIII transition metal compound, a hydride source and a reagent that can contribute a substituent to form a substituted bicycIo[1.1.1 ]pentane, such as a compound of the general Formula (I).

Description

[0001] Incorporated by reference to any priority application [0002] Any and all applications on the basis of which a foreign priority claim or a domestic priority claim is made (eg, as set forth in the Application Data Sheet or Request filed with this application) pursuant to 37 CFR 1.57, and Regulations 4.18 and 20.6, are hereby incorporated by reference. into this article. technical field [0003] The present disclosure relates to synthetic organic chemistry, and in particular to [1.1.1]-dicyclopentane-based compounds (propane derivatives) and their synthesis. Background technique [0004] In synthetic organic chemistry, there is a significant need for new classes of small organic molecules for use as reagents. Although there are estimated to be 10 60 There are a wide variety of possible carbon-containing small molecules, but only a tiny fraction of them can be efficiently and efficiently synthesized using known reactions and readily available starting materials (or "b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C61/125C07C235/26C07C211/19
CPCC07C255/46C07C255/64C07C271/22C07C211/35C07C229/28C07C247/14C07C251/42C07C45/44C07C2602/38C07D249/06C07C47/347C07C253/30C07C253/32C07F15/02C07F7/0896C07C209/48C07C31/137C07C29/00C07C209/26C07C211/19C07C227/04C07C249/04C07C251/40C07C253/00C07C255/31C07C255/47C07C269/00
Inventor 凯文·杜安·邦克
Owner RECURIUM IP HLDG LLC
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