(3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate

Base Information

• Chemical Name: (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate
• CAS No.: 1428535-20-9
• Molecular Formula: C₂₈H₃₉NO₃
• Molecular Weight: 437.623
• Mol file: 1428535-20-9.mol

Synonyms:(3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate

Chemical Property of (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate

There total 11 articles about (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-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: 74.0%

(1R,4aR,4bR,8aR,10aR)-methyl 8a-(cyanomethyl)-4a,7-dimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylate (1428535-14-1) + benzyl bromide (100-39-0) → (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate (1428535-20-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In hexane; N,N-dimethyl-formamide; at 90 ℃; Inert atmosphere;

DOI:10.1021/ol400385w

Reference yield: 56.0%

(3'S,4R,4aS,6aR,9S,11aR,11bS)-methyl 2'-benzyl-4,9,11b-trimethyldodecahydro-1H-spiro[6a,9-methanocyclohepta[a]naphthalene-8,3'-[1,2]oxaziridine]-4-carboxylate → (3S,6aS,8aS,9R,12aS,12bS)-methyl 5-benzyl-3,9,12a-trimethyl-4-oxotetradecahydro-1H-3,6amethanonaphtho[2,1-c]azocine-9-carboxylate (1428535-22-1) + (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate (1428535-20-9)

Guidance literature:

In toluene; for 1.5h; regioselective reaction; Microwave irradiation;

DOI:10.1021/ol400385w

Reference yield:

isosteviol (27975-19-5) → (3S,6aR,8aS,9R,12aS,12bR)-methyl 4-benzyl-3,9,12a-trimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate (1428535-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 18 h / 80 °C / Inert atmosphere; Reflux

2.1: hydroxylamine hydrochloride; potassium acetate / ethanol; dichloromethane / 1 h / 50 °C

3.1: thionyl chloride / chloroform / 10 h / 60 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; hexane / 90 °C / Inert atmosphere

With thionyl chloride; lithium hydroxide monohydrate; hydroxylamine hydrochloride; potassium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; 3.1: |Beckmann Rearrangement;

DOI:10.1021/ol400385w

upstream raw materials:

isosteviol

isosteviol methyl ester

(1R,4aR,4bR,8aR,10aR)-methyl 8a-(cyanomethyl)-4a,7-dimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylate

benzyl bromide