<3R-<1(S^*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one

Base Information

• Chemical Name: <3R-<1(S^*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one
• CAS No.: 128704-84-7
• Molecular Formula: C₂₆H₂₉F₃N₂O₄
• Molecular Weight: 490.522

Synonyms:

Chemical Property of <3R-<1(S^*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of <3R-<1(S^*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one

There total 7 articles about <3R-<1(S^*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-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:

(S)-(-)-1-methyl-2-chloromethylpyrrolidine hydrochloride (67824-38-8) → <3R-<1(S*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (128704-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, from 0 deg C to RT, 3 h

2: (N,N-dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; sodium hydride; In dichloromethane;

DOI:10.1021/jm00082a018

Reference yield:

(3S,4S-trans)-3-carboxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (S)-α-methylbenzylamine salt (111688-58-5) → <3R-<1(S*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (128704-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / KHCO₃ / dimethylformamide / 5.17 h / 0 - 20 °C

2: 1.) potassium hexamethyldisilazide, 2.) O₂, P(OEt)3 / 1.) THF, -70 deg C, 1 h, 2.) THF, 0 deg C, 2 h

3: 66 percent / LiI, H₂O / pyridine / 2 h / Heating

4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, from 0 deg C to RT, 3 h

5: (N,N-dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; water; oxygen; potassium hexamethylsilazane; sodium hydride; potassium hydrogencarbonate; lithium iodide; triethyl phosphite; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00082a018

Reference yield:

(3R-cis)-3-(hydroxy)-1,3,4,5-tetrahydro-4-[4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (127061-43-2) → <3R-<1(S*),3α,4α>>-3-(acetyloxy)-1-<(1-methyl-2-pyrrolidinyl)methyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (128704-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, from 0 deg C to RT, 3 h

2: (N,N-dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; sodium hydride; In dichloromethane;

DOI:10.1021/jm00082a018

upstream raw materials:

acetic anhydride

<3R-<1(S^*),3α,4α>>-1-<(1-methyl-2-pyrrolidinyl)methyl>-3-hydroxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one

(S)-(-)-1-methyl-2-chloromethylpyrrolidine hydrochloride

(3S,4S-trans)-3-carboxy-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (S)-α-methylbenzylamine salt

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