2,7-Diazaspiro[4.5]decane-2,3-dicarboxylic acid, 10-[2-(1,1-dimethylethoxy)-2-oxoethyl]-7-[(4-methoxyphenyl)methyl]-1,6- dioxo-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R,5R,10S)-

Base Information

• Chemical Name: 2,7-Diazaspiro[4.5]decane-2,3-dicarboxylic acid, 10-[2-(1,1-dimethylethoxy)-2-oxoethyl]-7-[(4-methoxyphenyl)methyl]-1,6- dioxo-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R,5R,10S)-
• CAS No.: 398476-16-9
• Molecular Formula: C29H40N2O9
• Molecular Weight: 560.645
• Mol file: 398476-16-9.mol

Synonyms:

Chemical Property of 2,7-Diazaspiro[4.5]decane-2,3-dicarboxylic acid, 10-[2-(1,1-dimethylethoxy)-2-oxoethyl]-7-[(4-methoxyphenyl)methyl]-1,6- dioxo-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R,5R,10S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,7-Diazaspiro[4.5]decane-2,3-dicarboxylic acid, 10-[2-(1,1-dimethylethoxy)-2-oxoethyl]-7-[(4-methoxyphenyl)methyl]-1,6- dioxo-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R,5R,10S)-

There total 7 articles about 2,7-Diazaspiro[4.5]decane-2,3-dicarboxylic acid, 10-[2-(1,1-dimethylethoxy)-2-oxoethyl]-7-[(4-methoxyphenyl)methyl]-1,6- dioxo-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R,5R,10S)- 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: 80.0%

(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester (398476-15-8) → (3R, 5R, 10R)-10-(tert-butoxycarbonylmethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane-2,3-dicarboxylic 2-tert-butyl ester 3-methyl ester (398476-16-9)

Guidance literature:

(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester; With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 16h; Heating;

With hydrogen; palladium on activated charcoal; In methanol; for 16h; under 760 Torr;

DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

Reference yield:

1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate (128811-48-3) → (3R, 5R, 10R)-10-(tert-butoxycarbonylmethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane-2,3-dicarboxylic 2-tert-butyl ester 3-methyl ester (398476-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 95 percent / tetrahydrofuran / -78 °C

2.1: 73 percent / AgOTf; (iPr)2NEt / acetonitrile / 14 h / 20 °C

3.1: (iPr)2NEt / acetonitrile / 16 h / Heating

3.2: 80 percent / H₂ / 10 percent Pd/C / methanol / 16 h / 760 Torr

With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

Reference yield:

N-(4-methoxybenzyl)-4-amino-1-butyne (146980-79-2) → (3R, 5R, 10R)-10-(tert-butoxycarbonylmethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane-2,3-dicarboxylic 2-tert-butyl ester 3-methyl ester (398476-16-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / DMAP; NEt₃ / CH₂Cl₂ / 72 h / 20 °C

2.1: nBuLi / diethyl ether; hexane / 0.5 h / -78 °C

2.2: 96 percent / diethyl ether; hexane / 1.25 h / -78 - 20 °C

3.1: 73 percent / pTsOH*H₂O / 2-methyl-propan-2-ol; diethyl ether / 16 h / 20 °C

4.1: 73 percent / AgOTf; (iPr)2NEt / acetonitrile / 14 h / 20 °C

5.1: (iPr)2NEt / acetonitrile / 16 h / Heating

5.2: 80 percent / H₂ / 10 percent Pd/C / methanol / 16 h / 760 Torr

With dmap; n-butyllithium; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

upstream raw materials:

(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate

N-(4-methoxybenzyl)-4-amino-1-butyne

N-(4-methoxybenzyl)-5-amino-1-pent-2-ynoic tert-butyl ester

Downstream raw materials:

(3R, 5S, 10R)-10-(tert-butoxycarbonylmethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane-3-carboxylic methyl ester

(3R, 5S, 10R)-10-(tert-butoxycarbonylmethyl)-2-(5-hexenyl)-7-(4-methoxybenzyl)-3-vinyl-1,6-dioxa-2,7-diaza-spiro[4,5]decane

(3R, 5S, 10R)-10-(tert-butoxycarbonylmethyl)-3-(2-hydroxymethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane

(3R, 5S, 10R)-10-(tert-butoxycarbonylmethyl)-7-(4-methoxybenzyl)-1,6-dioxa-2,7-diaza-spiro[4,5]decane-3-carboxaldehyde

Refernces