123387-51-9

Basic information

• Product Name: 4,4-(ETHYLENEDIOXY)-1-TERT-BUTOXYCARBONYLPIPERIDINE
• Synonyms: 4,4-(ETHYLENEDIOXY)-1-TERT-BUTOXYCARBONYLPIPERIDINE;N-BOC-1,4-DIOXA-8-AZA-SPIRO[4.5]DECANE;1,4-Dioxa-8-azaspiro[4.5]decane-8-carboxylic Acid 1,1-DiMethylethyl Ester;1-tert-Butoxycarbonyl-4-piperidone Ethylene Ketal;8-(tert-Butoxycarbonyl)-1,4-dioxa-8-azaspiro[4.5]decane;1-BOC-4,4-(ethylenedioxy)piperidine;tert-Butyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate
• CAS NO: 123387-51-9
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.29944
• Product Categories: Heterocycles series;Heterocycles;Miscellaneous Reagents
• Mol File: 123387-51-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 330.826 °C at 760 mmHg
• Flash Point: 153.878 °C
• Appearance: /
• Density: 1.145 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: 2-8°C
• Solubility: Methanol, Tetrahydrofuran
• CAS DataBase Reference: 4,4-(ETHYLENEDIOXY)-1-TERT-BUTOXYCARBONYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-(ETHYLENEDIOXY)-1-TERT-BUTOXYCARBONYLPIPERIDINE(123387-51-9)
• EPA Substance Registry System: 4,4-(ETHYLENEDIOXY)-1-TERT-BUTOXYCARBONYLPIPERIDINE(123387-51-9)

Safety Data

• Hazardous Substances Data: 123387-51-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

1,4-Dioxa-8-azaspiro[4.5]decane-8-carboxylic Acid 1,1-Dimethylethyl Ester (cas# 123387-51-9) is a compound useful in organic synthesis.

InChI:InChI=1/C12H21NO4/c1-11(2,3)17-10(14)13-6-4-12(5-7-13)15-8-9-16-12/h4-9H2,1-3H3

Upstream product

• 201230-82-2 carbon monoxide 
• 177-11-7 4,4-ethylenedioxy-piperidine 
• 75-65-0 tert-butyl alcohol 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 122-51-0 orthoformic acid triethyl ester 
• 111-46-6 diethylene glycol 
• 107-21-1 ethylene glycol 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 177-11-7 4,4-ethylenedioxy-piperidine 
• 681291-92-9 (+)-(2R-trans)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-(1-piperazinyl)piperidine 
• 681291-91-8 (+)-(2R-trans)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-[4-(phenylmethyl)-1-piperazinyl]piperidine 
• 717927-37-2 (+)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-piperidinone 
• 193201-63-7 (±)-7-(phenylmethyl)-1,4-dioxa-8-azaspiro[4.5]decane 
• 190964-86-4 (+/-)-1-[3,5-bis-(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-piperidinone 

Relevant articles and documents

Total synthesis of tropinone using 1,3-dipolar cycloaddition of cyclic azomethine ylide and phenyl vinyl sulfone as the key step

Total synthesis of tropinone from the readily available piperidone 2 is described. The rapid assembly of the tropane skeleton was achieved by 1,3-dipolar cycloaddition of cyclic azomethine ylide 3 to phenyl vinyl sulfone.

High-Temperature Boc Deprotection in Flow and Its Application in Multistep Reaction Sequences

A simplified Boc deprotection using a high-temperature flow reactor is described. The system afforded the qualitative yield of a wide variety of deprotected substrates within minutes using acetonitrile as the solvent and without the use of acidic conditions or additional workups. Highly efficient, multistep reaction sequences in flow are also demonstrated wherein no extraction or isolation was required between steps.

Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5] decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D

The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the ers were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.