(-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

Base Information

• Chemical Name: (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione
• CAS No.: 81504-95-2
• Molecular Formula: C₂₄H₂₅NO₅
• Molecular Weight: 407.466
• Mol file: 81504-95-2.mol

Synonyms:(-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

Chemical Property of (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

There total 3 articles about (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione 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: 94.0%

(-)-<3'S-3'α(S*),8'aβ>-8-benzyloxy-1-bromo-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione (81509-55-9) → (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione (81504-95-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In various solvent(s); at 70 ℃; for 14h;

DOI:10.1071/CH9841709

Reference yield:

Sodium; (S)-1-(8-benzyloxy-5-methoxy-3,4-dihydro-naphthalene-2-carbonyl)-pyrrolidine-2-carboxylate (93073-75-7) → (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione (81504-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS / dimethylformamide

2: Bu₃SnH, PhBr / 70 °C

With N-Bromosuccinimide; bromobenzene; tri-n-butyl-tin hydride; In N,N-dimethyl-formamide;

DOI:10.1039/c39810001100

Reference yield:

C24H24BrNO5 → (-)-(3'S-cis)-8-benzyloxy-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione (81504-95-2) + C24H25NO5

Guidance literature:

With bromobenzene; tri-n-butyl-tin hydride; at 70 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/c39810001100

upstream raw materials:

(-)-<3'S-3'α(S^*),8'aβ>-8-benzyloxy-1-bromo-5-methoxy-3,4,6',7',8',8'a-hexahydrospiropyrrolo<2,1-c><1,4>oxazine>-1',4'-dione

Sodium; (S)-1-(8-benzyloxy-5-methoxy-3,4-dihydro-naphthalene-2-carbonyl)-pyrrolidine-2-carboxylate

Downstream raw materials:

(R)-(-)-2-Acetyl-5-methoxy-8-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-2-ol