tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

Base Information

• Chemical Name: tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate
• CAS No.: 1147557-97-8
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.277
• Hs Code.: 2934999090
• Mol file: 1147557-97-8.mol

Synonyms:2-azaspiro[3.3]heptane-2-carboxylic acid,6-hydroxy-,1,1-dimethylethyl ester;

Chemical Property of tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

Chemical Property:

• Melting Point: 127-129℃
• Boiling Point: 316.6±42.0 °C(Predicted)
• PKA: 14.84±0.20(Predicted)
• Density: 1.17
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-?Butyl6-?Hydroxy-?2-?azaspiro[3.3]?heptane-?2-?carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-?Butyl 6-?Hydroxy-?2-?azaspiro[3.3]?heptane-?2-?carboxylate is a reactant used in the synthesis of pharmaceuticals such as CNS penetrant CXCR2 antagonists for the potential treatment of CNS demyelinating.

Technology Process of tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

There total 7 articles about tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1181816-12-5) → 6-hydroxy-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1147557-97-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;

Reference yield:

6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1181816-12-5) → 6-hydroxy-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1147557-97-8) + tert-butyl 7-oxo-6-oxa-2-azaspiro[3.4]octane-2-carboxylate

Guidance literature:

With alpha-D-glucopyranose; glucose dehydrogenase (GDH-105); Baeyere-Villiger monooxygenase P₃-C₀₇; oxygen; NADPH; In methanol; aq. phosphate buffer; at 30 ℃; for 24h; pH=9; Enzymatic reaction;

DOI:10.1016/j.tet.2015.12.071

Reference yield:

tert-butyl 6-(benzyloxy)-2-azaspiro[3.3]heptane-2-carboxylate (1181816-16-9) → 6-hydroxy-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1147557-97-8)

Guidance literature:

With cyclohexa-1,4-diene; 20 % Pd(OH)2/C; In methanol; for 48h; Reflux;

DOI:10.1021/ol901325s

upstream raw materials:

tert-butyl 6-(benzyloxy)-2-azaspiro[3.3]heptane-2-carboxylate

5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester

6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester

1-(6-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-1-one

tert-butyl 6-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate

3-(4-phenoxyphenyl)-1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Refernces

• 1、 Nóvoa, Luis,Trulli, Laura,Parra, Alejandro,Tortosa, Mariola. "Stereoselective Diboration of Spirocyclobutenes: A Platform for the Synthesis of Spirocycles with Orthogonal Exit Vectors". supporting information. p. 11763 - 11768. Retrieved 2021/04/26.
• 2、 -. "TARGETING COMPOUNDS". Paragraph 0271. . Retrieved 2019/07/19.