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1-t-Boc-piperidine-4-spiro-5'-hydantoin

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1-t-Boc-piperidine-4-spiro-5'-hydantoin Basic information
Product Name:1-t-Boc-piperidine-4-spiro-5'-hydantoin
Synonyms:2,4-Dioxo-1,3,8-triazaspiro[4.5]decane, N8-BOC protected;tert-Butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate, 8-(tert-Butoxycarbonyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane;8-tert-Butoxycarbonyl-1,3,8-triazaspiro[4.5]decane-2,4-dione;8-Boc-2,4-dioxo-1,3,8-triazaspiro[4.5]decane;2,4-Dioxo-1,3-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester;2,4-diketo-1,3,8-triazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester;2,4-Dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylic Acid 1,1-DiMethylethyl Ester;2,4-Dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester
CAS:183673-70-3
MF:C12H19N3O4
MW:269.3
EINECS:
Product Categories:Amino Acids & Derivatives;Hydantoins & Derivatives
Mol File:Mol File
1-t-Boc-piperidine-4-spiro-5'-hydantoin Structure
1-t-Boc-piperidine-4-spiro-5'-hydantoin Chemical Properties
Melting point 242-244°C
density 1.28±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Dichloromethane, DMSO, Methanol
form Solid
pka10.10±0.20(Predicted)
color White to Off-White
InChIInChI=1S/C12H19N3O4/c1-11(2,3)19-10(18)15-6-4-12(5-7-15)8(16)13-9(17)14-12/h4-7H2,1-3H3,(H2,13,14,16,17)
InChIKeyDHJXKTPWDXJQEK-UHFFFAOYSA-N
SMILESN1C2(CCN(C(OC(C)(C)C)=O)CC2)C(=O)NC1=O
CAS DataBase Reference183673-70-3
Safety Information
HS Code 2933599590
MSDS Information
1-t-Boc-piperidine-4-spiro-5'-hydantoin Usage And Synthesis
Chemical PropertiesOff-White Powder
UsesA cyclic α,α-disubstituted amino acid for preparation of water-soluble highly helical peptides.
UsesA cyclic a,a-disubstituted amino acid for preparation of water-soluble highly helical peptides
Synthesis
POTASSIUM CYANIDE

151-50-8

Ammonium carbonate

506-87-6

N-(tert-Butoxycarbonyl)-4-piperidone

79099-07-3

1-T-BOC-PIPERIDINE-4-SPIRO-5'-HYDANTOIN

183673-70-3

An aqueous solution (50 mL) of potassium cyanide (22.5 g, 0.335 mol) was slowly added dropwise over a period of 5 minutes to a mixture of water (90 mL) and methanol (110 mL) containing N-tert-butoxycarbonyl-4-piperidone (32.48 g, 0.1598 mol) and ammonium carbonate (33.8 g, 0.351 mol). Upon completion of the dropwise addition, an off-white precipitate rapidly appeared in the reaction mixture. Subsequently, the reaction flask was sealed and the suspension was stirred continuously at room temperature for 72 hours. Upon completion of the reaction, the light yellow precipitate was collected by filtration and washed with a small amount of water to afford 8-Boc-2,4,8-triazaspiro[4.5]decane-1,3-dione (37.1 g, 86% yield) as a colorless solid.

References[1] Patent: WO2009/64274, 2009, A1. Location in patent: Page/Page column 15
[2] Patent: WO2007/139813, 2007, A1. Location in patent: Page/Page column 17
[3] Patent: US2005/261322, 2005, A1. Location in patent: Page/Page column 19
[4] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2687 - 2692
1-t-Boc-piperidine-4-spiro-5'-hydantoin Preparation Products And Raw materials
Raw materialsPOTASSIUM CYANIDE-->Ammonium carbonate-->N-(tert-Butoxycarbonyl)-4-piperidone
Tag:1-t-Boc-piperidine-4-spiro-5'-hydantoin(183673-70-3) Related Product Information
1,3,8-Triaza-spiro[4.5]decane-2,4-dione 8-Benzyl-1,3,8-triazaspiro[4.5]decane-2,4-dione 1-t-Boc-piperidine-4-spiro-5'-[1',3'-bis-t-Boc]-hydantoin 8-triazaspiro(4.5)decane-2,4-dione,8-methyl-3 1,3,8-Triaza-spiro[4.5]decane-2,4-dione hydrochloride 3-Benzyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione