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

Base Information

• Chemical Name: tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate
• CAS No.: 1181816-12-5
• Molecular Formula: C11H17NO3
• Molecular Weight: 211.261
• Hs Code.: 2933990090
• Mol file: 1181816-12-5.mol

Synonyms:tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate;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

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

Chemical Property:

• Melting Point: 114.5-116 °C
• Boiling Point: 314.7±42.0 °C(Predicted)
• PKA: -0.93±0.20(Predicted)
• PSA: 46.61000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 1.52430
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

tert-?Butyl6-?Oxo-?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-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.

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

There total 4 articles about tert-butyl 6-oxo-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: 73.0%

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

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.666667h;

DOI:10.1021/ol901325s

Reference yield: 66.0%

5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1239320-10-5) → 6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1181816-12-5)

Guidance literature:

With ammonium chloride; zinc; In methanol; at 20 ℃; for 18h; Inert atmosphere;

Reference yield:

3-methylene-azetidine-1-carboxylic acid tert-butyl ester (934664-41-2) → 6-oxo-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (1181816-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc-copper amalgam / 1,2-dimethoxyethane / 12 h / 0 - 20 °C

2: zinc; ammonium chloride / methanol / 12 h / 20 °C / Cooling with ice

With ammonium chloride; zinc; zinc-copper amalgam; In methanol; 1,2-dimethoxyethane;

upstream raw materials:

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

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

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

3-methylazetidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "Sulfonamide derivative and application thereof in pharmacy". Paragraph 0176; 0177; 0178. . Retrieved 2017/05/02.
• 2、 -. "7-AZA-SPIRO[3.5]NONANE-7-CARBOXYLATE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF". Page/Page column 13. . Retrieved 2012/06/01.