tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate
• CAS No.: 1349199-63-8
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Hs Code.: 2934999090
• Mol file: 1349199-63-8.mol

Synonyms:tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate;6-Boc-1-oxa-6-azaspiro[3.3]heptan-3-ol

Chemical Property of tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate

Chemical Property:

• Boiling Point: 344.8±42.0 °C(Predicted)
• PKA: 14.00±0.20(Predicted)
• PSA: 59.00000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 0.30490
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Spirocyclic building block is part of a series of advanced angular[3.3]heptanes developed by Carreira and coworkers

Technology Process of tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate

There total 4 articles about tert-Butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-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: 99.0%

tert-butyl 3-oxo-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate (1349199-61-6) → tert-butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate (1349199-63-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1021/ol2028459

Reference yield:

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) → tert-butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate (1349199-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.25 h / -78 °C / Inert atmosphere

1.2: 1.28 h / -78 - -20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.1: 8-ethyl quinoline N-oxide; methanesulfonic acid / 1,1-dichloroethane / 3 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; methanesulfonic acid; 8-ethyl quinoline N-oxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; hexanes; 1,1-dichloroethane;

DOI:10.1021/ol2028459

Reference yield:

tert-butyl 3-ethynyl-3-hydroxy-azetidine-1-carboxylate (1259034-35-9) → tert-butyl 3-hydroxy-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate (1349199-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 8-ethyl quinoline N-oxide; methanesulfonic acid / 1,1-dichloroethane / 3 h / 20 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; methanesulfonic acid; 8-ethyl quinoline N-oxide; In methanol; 1,1-dichloroethane;

DOI:10.1021/ol2028459

upstream raw materials:

tert-butyl 3-oxoazetidine-1-carboxylate

tert-butyl 3-ethynyl-3-hydroxy-azetidine-1-carboxylate

tert-butyl 3-oxo-1-oxa-6-azaspiro[3.3]heptane-6-carboxylate

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