tert-butyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate

Base Information

• Chemical Name: tert-butyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate
• CAS No.: 908264-55-1
• Molecular Formula: C₂₀H₂₈N₂O₃
• Molecular Weight: 344.454
• Mol file: 908264-55-1.mol

Synonyms:(5R)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester

Chemical Property of tert-butyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate

Chemical Property:

• Vapor Pressure: 4.74E-10mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate

There total 7 articles about tert-butyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazaspiro[4.4]nonane-1-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:

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate (850426-34-5) → (5R)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (908264-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 20 °C

1.2: magnesium sulfate / methanol / 20 °C

1.3: NaBH₄ / methanol / 20 °C

2.1: sodium amide / toluene / Heating

With sodium amide; In methanol; toluene;

DOI:10.1016/j.tet.2007.06.050

Reference yield:

2-[2-(1-phenyl-ethylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → (5R)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (908264-55-1) + (5S)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (908264-65-3)

Guidance literature:

With sodium amide; In toluene; Heating;

DOI:10.1016/j.tetlet.2006.05.154

Reference yield:

methyl (2S)-pyrrolidine carboxylate (2577-48-2) → (5R)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester (908264-55-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 74 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: LiHMDS / tetrahydrofuran / -78 °C

2.2: 80 percent / tetrahydrofuran / 20 °C

3.1: 74 percent / OsO₄; NaIO₄; H₂O / tetrahydrofuran / 20 °C

4.1: methanol / 20 °C

4.2: magnesium sulfate / methanol / 20 °C

4.3: NaBH₄ / methanol / 20 °C

5.1: sodium amide / toluene / Heating

With dmap; sodium periodate; osmium(VIII) oxide; water; sodium amide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/j.tet.2007.06.050

upstream raw materials:

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate

methyl (2S)-pyrrolidine carboxylate

(S)-N-(tert-butoxycarbonyl)proline methyl ester

L-proline

Downstream raw materials:

(5R)-6-oxo-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane

(5R)-7-((S)-1'-phenylethyl)-1,7-diazaspiro[4.4]nonane