4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester

Base Information

• Chemical Name: 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester
• CAS No.: 827614-08-4
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.419
• Mol file: 827614-08-4.mol

Synonyms:4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester

Chemical Property of 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester

There total 2 articles about 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester 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: 57.0%

4-(dimethylamino)benzoyl chloride (4755-50-4) + (+)-(1S,8S)-1,2,3,6,7,8-hexahydro-as-indacene-1,8-diol (827614-05-1) → 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester (827614-08-4) + C30H32N2O4

Guidance literature:

With dmap; In tetrahydrofuran; at 60 ℃; for 24h;

DOI:10.1016/j.tetlet.2004.11.028

Reference yield:

2,3,6,7-tetrahydro-as-indacene-1,8-dione (17833-66-8) → 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester (827614-08-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / HCOOH; Et3N; (S,S)-Ts-DPEN / [RuCl2(η⁶-cymene)]2 / dimethylformamide / 54 h / 20 °C

2: NaBH₄ / methanol

3: 38 percent / DMAP / tetrahydrofuran / 24 h / 60 °C

With dmap; sodium tetrahydroborate; formic acid; triethylamine; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.11.028

Reference yield: 72.0%

acetic anhydride (108-24-7) + 4-Dimethylamino-benzoic acid (1S,8S)-8-hydroxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester (827614-08-4) → 4-Dimethylamino-benzoic acid (1S,8S)-8-acetoxy-1,2,3,6,7,8-hexahydro-as-indacen-1-yl ester

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.028

upstream raw materials:

4-(dimethylamino)benzoyl chloride

(+)-(1S,8S)-1,2,3,6,7,8-hexahydro-as-indacene-1,8-diol

2,3,6,7-tetrahydro-as-indacene-1,8-dione