tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

Base Information

• Chemical Name: tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate
• CAS No.: 474397-68-7
• Molecular Formula: C₃₅H₄₄N₄O₅
• Molecular Weight: 600.758
• Mol file: 474397-68-7.mol

Synonyms:tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

Chemical Property of tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate

There total 3 articles about tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-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:

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (72821-79-5) → tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate (474397-68-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C

2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C

3: NaHMDS / tetrahydrofuran / -40 - 20 °C

With 2-hydroxypyridin; dmap; sodium hexamethyldisilazane; In tetrahydrofuran; ethylene glycol;

DOI:10.1021/jo0203847

Reference yield:

1-amino-3-(dimethylamino)propane (109-55-7) → tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate (474397-68-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 2-hydroxypyridine / ethane-1,2-diol / 18 h / 100 °C

2: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C

3: NaHMDS / tetrahydrofuran / -40 - 20 °C

With 2-hydroxypyridin; dmap; sodium hexamethyldisilazane; In tetrahydrofuran; ethylene glycol;

DOI:10.1021/jo0203847

Reference yield:

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide (85329-86-8) → tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl](phenoxycarbonyl)amino]carbonyl]ergoline-1-carboxylate (474397-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 40 °C

2: NaHMDS / tetrahydrofuran / -40 - 20 °C

With dmap; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo0203847

upstream raw materials:

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

1-amino-3-(dimethylamino)propane

Downstream raw materials:

cabergoline

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate