6,9-Diazaspiro[4.5]decane-9-acetic acid, 8-(3,5-difluorophenyl)-10-oxo-, (8R)-

Base Information

• Chemical Name: 6,9-Diazaspiro[4.5]decane-9-acetic acid, 8-(3,5-difluorophenyl)-10-oxo-, (8R)-
• CAS No.: 957187-34-7
• Molecular Formula: C16H18F2N2O3
• Molecular Weight: 324.327
• Mol file: 957187-34-7.mol

Synonyms:6,9-DIAZASPIRO[4.5]DECANE-9-ACETIC ACID, 8-(3,5-DIFLUOROPHENYL)-10-OXO-, (8R)-;

Chemical Property of 6,9-Diazaspiro[4.5]decane-9-acetic acid, 8-(3,5-difluorophenyl)-10-oxo-, (8R)-

Chemical Property:

• Boiling Point: 529.1±50.0 °C (760 mmHg)
• PSA: 69.64000
• Density: 1.39±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 2.10180

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6,9-Diazaspiro[4.5]decane-9-acetic acid, 8-(3,5-difluorophenyl)-10-oxo-, (8R)-

There total 23 articles about 6,9-Diazaspiro[4.5]decane-9-acetic acid, 8-(3,5-difluorophenyl)-10-oxo-, (8R)- 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%

ethyl [(8R)-8-(3,5-difluorophenyl)-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]acetate (957121-89-0) → C16H18F2N2O3 (957187-34-7)

Guidance literature:

ethyl [(8R)-8-(3,5-difluorophenyl)-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]acetate; With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h; Industry scale;

With hydrogenchloride; In tetrahydrofuran; water; Industry scale;

With sodium acetate; In water; at 20 ℃; pH=4.5; Industry scale;

Reference yield:

cycloleucine methyl ester hydrochloride (60421-23-0) → C16H18F2N2O3 (957187-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium phosphate / N,N-dimethyl-formamide / -15 - 5 °C / Industry scale; Inert atmosphere

1.2: Industry scale; Inert atmosphere

2.1: hydrogen; methanesulfonic acid / ((-)-(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride / methanol / 18 h / 80 °C / 20686.5 Torr / Industry scale

3.1: N-ethyl-N,N-diisopropylamine / methanol / pH 6 / Industry scale

4.1: thionyl chloride; N-ethyl-N,N-diisopropylamine / toluene / -35 - -20 °C / Industry scale

5.1: sodium periodate / toluene; acetonitrile; water / 15 - 25 °C / Aqueous phosphate buffer; Industry scale

6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; acetonitrile / 20 °C / Industry scale

6.2: 70 °C / Industry scale

6.3: pH 8 / Industry scale

7.1: water; lithium hydroxide / tetrahydrofuran / 2 h / 10 °C

7.2: 0 °C / pH < 1

7.3: 85 °C

With potassium phosphate; sodium periodate; thionyl chloride; methanesulfonic acid; water; hydrogen; N-ethyl-N,N-diisopropylamine; lithium hydroxide; ((-)-(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

4-(3,5-difluorophenyl)-5H-[1,2,3]-oxathiazole 2,2-dioxide (1260403-64-2) → C16H18F2N2O3 (957187-34-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen / palladium diacetate; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / methanol / 16 h / 40 °C / 4137.29 Torr / Autoclave

2.1: potassium phosphate / water

2.2: 21 h / 50 - 70 °C

3.1: hydrogenchloride / sulfolane; water / 60 °C

4.1: sodium hydroxide / sulfolane; water / 20 - 60 °C / pH 10

5.1: sodium hexamethyldisilazane / tetrahydrofuran / -20 - -10 °C

5.2: -15 - -10 °C

6.1: water; lithium hydroxide / tetrahydrofuran / 2 h / 10 °C

6.2: 0 °C / pH < 1

6.3: 85 °C

With hydrogenchloride; potassium phosphate; water; hydrogen; sodium hexamethyldisilazane; sodium hydroxide; lithium hydroxide; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; sulfolane; methanol; water;

upstream raw materials:

3,5-difluorobromobenzene

2-bromo-1-(3,5-difluorophenyl)ethanone

cycloleucine methyl ester hydrochloride

ethyl [(8R)-8-(3,5-difluorophenyl)-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]acetate

Downstream raw materials:

[3H]-MK 3207

Refernces

• 1、 -. "PROCESS FOR MAKING CGRP RECEPTOR ANTAGONIST". . . Retrieved 2011/02/24.