tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate

Base Information

• Chemical Name: tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate
• CAS No.: 1101840-74-7
• Molecular Formula: C₁₂H₁₉NO₃
• Molecular Weight: 225.288
• Mol file: 1101840-74-7.mol

Synonyms:

Chemical Property of tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate

Chemical Property:

• Boiling Point: 331.8±35.0 °C(Predicted)
• PKA: -1.81±0.20(Predicted)
• Density: 1.14±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl4-Oxo-6-azaspiro[2.5]octane-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-oxo-6-azaspiro[2.5]octane-6-carboxylate

There total 2 articles about tert-butyl 4-oxo-6-azaspiro[2.5]octane-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: 89.0%

tert-butyl 4-hydroxy-6-azaspiro[2.5]octane-6-carboxylate (1101840-72-5) → 4-Oxo-6-aza-spiro[2,5]octane-6-carboxylic acid tert-butyl ester (1101840-74-7)

Guidance literature:

tert-butyl 4-hydroxy-6-azaspiro[2.5]octane-6-carboxylate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -70 - -60 ℃; for 2.25h;

With triethylamine; In dichloromethane; at -60 ℃; for 1.18333h; Product distribution / selectivity;

Reference yield:

3-hydroxy-4-methylene-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (159635-22-0) → 4-Oxo-6-aza-spiro[2,5]octane-6-carboxylic acid tert-butyl ester (1101840-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethylzinc / toluene; 1,2-dichloro-ethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -70 - -60 °C

2.2: 0.17 h / -60 °C

With oxalyl dichloride; diethylzinc; dimethyl sulfoxide; In dichloromethane; 1,2-dichloro-ethane; toluene; 2.1: Swern Oxidation / 2.2: Swern Oxidation;

Reference yield:

4-Oxo-6-aza-spiro[2,5]octane-6-carboxylic acid tert-butyl ester (1101840-74-7) → 4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester (1290048-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; magnesium(II) chloride hexahydrate; α-D-glucose monohydrate / ketoreductase KRED-NADH-117; glucose dehydrogenase GDH-102 / 35 °C / pH 6.5 / Aqueous buffer

2.1: hydrogenchloride / 1,4-dioxane; ethanol / 1 h / 20 °C

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / acetonitrile; water / 0 - 20 °C

3.2: 16 h

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; magnesium(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; α-D-glucose monohydrate; sodium hydroxide; ketoreductase KRED-NADH-117; glucose dehydrogenase GDH-102; In 1,4-dioxane; ethanol; water; acetonitrile;

upstream raw materials:

tert-butyl 4-hydroxy-6-azaspiro[2.5]octane-6-carboxylate

3-hydroxy-4-methylene-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

Downstream raw materials:

(S)-6-aza-spiro[2.5]octan-4-ol hydrochloride

4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

(S)-4-[(R,S)-3-Hydroxy-4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

(S)-4-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-3-oxo-propyl]-3-methyl-piperazin-2-one

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