tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

Base Information

Chemical Name:tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate
CAS No.:742075-06-5
Molecular Formula:C₃₀H₃₈N₂O₅
Molecular Weight:506.642
Hs Code.:

tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

Synonyms:tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

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Chemical Property of tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

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Technology Process of tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

There total 8 articles about tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-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: 84.0%

: 103-67-3
benzyl-methyl-amine

: 742075-03-2
tert-butyl (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-7-oxo-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

: 742075-06-5
tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

Guidance literature:: benzyl-methyl-amine; tert-butyl (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-7-oxo-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate; With toluene-4-sulfonic acid; benzoic acid; In benzene; for 18h; Reflux; Dean-Stark; Inert atmosphere;

With sodium cyanoborohydride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 2.5h; Inert atmosphere; Molecular sieve;
DOI:10.1021/acs.jmedchem.6b01418

Reference yield:

: 52446-25-0
noroxyoxycodone hydrochloride

: 742075-06-5
tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / aq. NaHCO₃ / CHCl₃ / 3 h / 20 °C

2.1: PhCO₂H / 19 h / Heating

2.2: 72 percent / NaBH₃CN / methanol / 2 h / 0 °C

With sodium hydrogencarbonate; benzoic acid; In chloroform;
DOI:10.1248/cpb.52.670

Reference yield:

: 16676-29-2
naltrexone Hydrochloride

: 742075-06-5
tert-butyl (4R,4aS,7R,7aR,12bS)-7-[benzyl(methyl)amino]-4a-hydroxy-9-methoxy-1,2,4,4a,5,6,7,7a-octahydro-3H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 11 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / toluene / 17 h / Dean-Stark; Inert atmosphere; Reflux

3.1: 1 h / Inert atmosphere; Reflux

4.1: potassium carbonate / 1,1,2,2-tetrachloroethane / 14 h / 140 °C / Inert atmosphere

5.1: potassium hydroxide / water; dimethyl sulfoxide / 6 h / 110 °C / Inert atmosphere

6.1: hydrogenchloride / water / 15 h / 80 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

8.1: toluene-4-sulfonic acid; benzoic acid / benzene / 18 h / Reflux; Dean-Stark; Inert atmosphere

8.2: 2.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

With hydrogenchloride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; benzoic acid; potassium hydroxide; In dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1,1,2,2-tetrachloroethane; benzene;
DOI:10.1021/acs.jmedchem.6b01418