(11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Base Information

• Chemical Name: (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
• CAS No.: 849795-72-8
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.406
• Mol file: 849795-72-8.mol

Synonyms:(11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Chemical Property of (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

There total 20 articles about (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 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: 70.0%

(11aS)-8-(benzyloxy)-1,2,3,10,11,11a-hexahydro-7-methoxy-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5,11-dione (132622-12-9) → (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (849795-72-8)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In various solvent(s); Heating;

DOI:10.1021/jo047872u

Reference yield:

4-(benzyloxy)-3-methoxybenzoic acid (1486-53-9) → (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (849795-72-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 58.6 percent / potassium carbonate / acetone / 3 h / Heating

2.1: 82.6 percent / nitric acid / tin(IV) chloride / CH₂Cl₂ / 0.17 h / -20 °C

3.1: 95.8 percent / sodium borohydride / nickel(II) chloride hexahydrate / methanol; CH₂Cl₂ / 0.5 h / 0 - 5 °C

4.1: 98 percent / aq. sodium hydroxide / methanol / 1 h / Heating

5.1: 81.1 percent / toluene / aq. NaOH / 2 h / 20 °C

6.1: 87.3 percent / sodium hydride / N,N-dimethyl-acetamide / 12 h / 20 °C

7.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

8.1: 0.31 g / triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

9.1: ozone / CH₂Cl₂; methanol / 0.08 h

9.2: dimethyl sulfide / CH₂Cl₂; methanol / 2 h / -78 - 20 °C

10.1: 0.064 g / camphorsulfonic acid / benzene / Heating

11.1: 91 percent / tributyltin hydride; AIBN / benzene / 2 h / Heating

12.1: potassium carbonate / acetonitrile; H₂O / 20 °C

With sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); nitric acid; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; ozone; triethylamine; toluene; camphor-10-sulfonic acid; tin(IV) chloride; nickel dichloride; In methanol; sodium hydroxide; dichloromethane; N,N-dimethyl acetamide; water; acetone; acetonitrile; benzene;

DOI:10.1021/ol991100g

Reference yield:

8-benzyloxy-7-methoxy-10-trifluoroacetyl-1,2,3,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one → (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (849795-72-8)

Guidance literature:

With potassium carbonate; In water; acetonitrile; at 20 ℃;

DOI:10.1021/ol991100g

upstream raw materials:

N-<2-Azido-4-(benzyloxy)-5-methoxybenzoyl>-L-proline methyl ester

(11aS)-8-(benzyloxy)-1,2,3,10,11,11a-hexahydro-7-methoxy-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5,11-dione

2-(allyl-trifluoroacetyl)-amino-4-benzyloxy-N-3-(bromopropyl)-5-methoxy-benzamide

8-benzyloxy-4-(3-bromopropyl)-7-methoxy-1-trifluoroacetyl-1,4-dihydrobenzo[e][1,4]diazepin-5-one

Downstream raw materials:

8-benzyl DC-81

(11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one