tert-Butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2-carboxylate

Base Information

• Chemical Name: tert-Butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2-carboxylate
• CAS No.: 1408074-46-3
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.276
• Hs Code.: 2934999090
• Mol file: 1408074-46-3.mol

Synonyms:tert-butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2- carboxylate

Chemical Property of tert-Butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2-carboxylate

Chemical Property:

• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2-Boc-5-hydroxy-7-oxo-2-azaspiro[3.4]octane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Spirocyclic building block was first synthesized by Carreira and coworkers, which provides a new area of chemical space with straightforward functional handles for further diversification.

Technology Process of tert-Butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2-carboxylate

There total 4 articles about tert-Butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-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: 92.0%

tert-butyl 7-oxo-5-oxa-2-azaspiro[3.4]octane-2-carboxylate (1408075-90-0) → tert-butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2- carboxylate (1408074-46-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h;

DOI:10.1021/ol402127b

Reference yield:

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) → tert-butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2- carboxylate (1408074-46-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 6 h / Inert atmosphere; Schlenk technique; Reflux

2.1: sodium hydride / mineral oil; diethyl ether / 0.5 h / 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sodium chloride / water; dimethyl sulfoxide / 2 h / 120 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

With sodium tetrahydroborate; sodium hydride; sodium chloride; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; mineral oil; 1.1: |Wittig Olefination / 3.1: |Krapcho Dealkoxycarbonylation;

DOI:10.1021/ol402127b

Reference yield:

2-(tert-butyl) 8-ethyl 7-oxo-5-oxa-2-azaspiro[3.4]octane-2,8-dicarboxylate (1453315-80-4) → tert-butyl 7-hydroxy-5-oxa-2-azaspiro[3.4]octane-2- carboxylate (1408074-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium chloride / water; dimethyl sulfoxide / 2 h / 120 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 2 h / 0 °C

With sodium tetrahydroborate; sodium chloride; In methanol; water; dimethyl sulfoxide; 1: |Krapcho Dealkoxycarbonylation;

DOI:10.1021/ol402127b

upstream raw materials:

tert-butyl 3-oxoazetidine-1-carboxylate

2-(tert-butyl) 8-ethyl 7-oxo-5-oxa-2-azaspiro[3.4]octane-2,8-dicarboxylate

tert-butyl 7-oxo-5-oxa-2-azaspiro[3.4]octane-2-carboxylate

tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate

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