5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Base Information

• Chemical Name: 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS No.: 192513-68-1
• Molecular Formula: C₁₈H₂₁NO₃S
• Molecular Weight: 331.436

Synonyms:5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property of 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

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Technology Process of 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

There total 2 articles about 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 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%

5-methylene-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine → 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (192513-68-1)

Guidance literature:

5-methylene-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 7h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.3987/COM-02-S(M)25

Reference yield:

1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (24310-36-9) → 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (192513-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 20 °C

2.1: borane-methyl sulfide complex / tetrahydrofuran / 7 h / 20 °C

2.2: 100 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 20 °C

With dimethylsulfide borane complex; potassium tert-butylate; In tetrahydrofuran; 1.1: Wittig reaction;

DOI:10.3987/COM-02-S(M)25

Reference yield: 47.0%

vinyl acetate (108-05-4,9003-20-7) + 5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (192513-68-1) → (S)-(+)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (192513-69-2) + (R)-(-)-[1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl]methyl acetate + acetic acid 1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ylmethyl ester

Guidance literature:

With Lipase QL; In di-isopropyl ether; ethyl acetate; at 0 - 5 ℃; for 4h;

DOI:10.3987/COM-02-S(M)25

upstream raw materials:

1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

Downstream raw materials:

(S)-(+)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

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