(+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

Base Information

• Chemical Name: (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione
• CAS No.: 125326-16-1
• Molecular Formula: C₁₉H₁₈N₂O₃
• Molecular Weight: 322.364

Synonyms:(+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

Chemical Property of (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

There total 7 articles about (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-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: 100.0%

benzyl bromide (100-39-0) + 9-hydroxy-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione → (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione (125326-16-1)

Guidance literature:

With potassium carbonate; In acetonitrile; at 0.7 ℃; for 0.12h; Inert atmosphere;

DOI:10.1074/jbc.M117.791558

Reference yield: 84.0%

8-(benzyloxy)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (125299-61-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione (125326-16-1)

Guidance literature:

In dimethyl sulfoxide; at 110 ℃; for 6h;

DOI:10.1016/S0040-4039(00)99602-3

Reference yield: 81.0%

8-(benzyloxy)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (125299-61-8) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → (+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione (125326-16-1)

Guidance literature:

In dimethyl sulfoxide; at 100 ℃; for 15h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201707737

upstream raw materials:

8-(benzyloxy)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione

L-proline

C₁₉H₂₀O₅

(S)-1-Pyrrolidin-2-yl-methanol

Downstream raw materials:

(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-(benzyloxycarbonyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

(S)-9-Benzyloxy-11-hydroxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carboxylic acid benzyl ester

(+)-(11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-(benzyloxycarbonyl)-11-hydroxy-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one

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