1181816-12-5

Basic information

• Product Name: tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate
• Synonyms: 6-Oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester;6-oxo-2-azaspiro[3.3]hept...;2-Boc-6-oxo-2-azaspiro[3....;2-Boc-6-oxo-2-azaspiro[3.3]heptane;tert-butyl 6-oxo-2-azaspiro[3.4]octane-2-carboxylate;2-Azaspiro[3.4]octane-2-carboxylic acid, 6-oxo-, 1,1-dimethylethyl ester;6-Oxo-2-azaspiro[3.3]heptane-2-carboxylic acid dimethylethyl ester;tert-Butyl 7-oxo-2-azaspiro[3.4]octane-2-carboxylate
• CAS NO: 1181816-12-5
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.25758
• Product Categories: 1363382-39-1 oldold;MFCD22421762 oldold
• Mol File: 1181816-12-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 114.5-116 °C
• Boiling Point: 314.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -0.93±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate(1181816-12-5)
• EPA Substance Registry System: tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate(1181816-12-5)

Safety Data

• Hazardous Substances Data: 1181816-12-5(Hazardous Substances Data)

Usage

Uses

tert-Butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate is a reagent used for the preparation of γ-butyrolactone derivative via Baeyer-Villiger monooxygenase (BVMO)-catalyzed oxidation.

Synthesis

A solution of crude tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (1.00 g,4.69mmol, 1.00 equiv) in dichloromethane(20 mL) was treated with Dess-Martin periodinane(2.10g,4.95 mmol, 1.06 equiv) in two batches a few min apart at 0 °C. After 10 min, the ice bath wasremoved, and the reaction was monitored by TLC (50% ethyl acetate, PMA stain). After 30 min.the reaction was diluted with ethyl acetate and washed twice with satd sodium bicarbonate. Theorganic layer was dried over sodium sulfate, filtered, and concentrated. The crude product waspurified by flash chromatography (80g silica gel, 10 to 50% ethyl acetate/heptane; pure fractionswere identified by TLC with PMA stain; an unidentified impurity elutes slightly earlier than theproduct) to give tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate as a white solid (721 mg,73%). mp 114.5-116C.

Upstream product

• 1147557-97-8 6-hydroxy-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester 
• 1239320-10-5 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester 
• 1314984-00-3 3-methylazetidine-1-carboxylic acid tert-butyl ester 
• 934664-41-2 3-methylene-azetidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1147557-97-8 6-hydroxy-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester 
• 1421270-66-7 C₂₂H₂₂Cl₂FN₅O*CH₂O₂ 
• 1421270-71-4 (±)-tert-butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate 
• 7631-86-9 SiO₂ 

Relevant articles and documents

CHEMICAL COMPOUNDS

The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. The compounds of the disclosure have activity as Janus kinase (JAK) inhibitors and are useful in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK by administering a compound herein described.

SELECTIVE OCTAHYDRO-CYCLOPENTA[C] PYRROLE NEGATIVE MODULATORS OF NR2B

Compounds that selectively negatively modulate NMDA receptors containing an NR1/NR2B subunit, pharmaceutical compositions comprising the compounds, and methods of treating a disease using the compounds are disclosed. Such diseases include, without limitation, neurological dysfunction such as Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, and seizure disorders; emotional disorders; depression; bipolar disorder; obsessive-compulsive disorder; and other anxiety disorders.

DERIVATIVES OF AZASPIRANYL-ALKYLCARBAMATES OF 5-MEMBER HETEROCYCLIC COMPOUNDS, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF

The invention relates to a compound of the general formula (I) in which R2 is a hydrogen or fluorine atom or a hydroxyl, cyano, trifluoromethyl, C1-6-alkyl, C1-6-alkoxy, NR8R9 group; m, n, o and p are independently an integer equal to 0, 1, 2 or 3; A is a covalent bond or a C1-8-alkylene group; R1 is an optionally substituted aryl or heteroaryl group; R3 is a hydrogen or fluorine atom or a C1-6-alkyl group or a trifluoromethyl group; R4 is an optionally substituted 5-member heterocyclic compound; the compound being in the form of a base or acid addition salt. The invention also relates to the therapeutic use thereof.