(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Base Information

Chemical Name:(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide
CAS No.:88204-61-9
Molecular Formula:C₂₁H₂₉NO₂
Molecular Weight:327.467
Hs Code.:

Synonyms:(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

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Chemical Property of (1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

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Technology Process of (1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

There total 12 articles about (1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide 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: 47.0%

: 2627-86-3
(S)-1-phenyl-ethylamine

: 76566-89-7,88244-69-3,78216-75-8,91109-68-1
(+/-)-1α-Ethyl-5β-(hydroxymethyl)-3aβ,4,5,7aα-tetrahydroindan-4β-carboxylic Acid γ-Lactone

: 88204-61-9
(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

: 88204-62-0
(1R,3aS,4R,5S,7aR)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Guidance literature:: With 2-hydroxypyridin; In toluene; at 110 ℃; for 6h;
DOI:10.1039/c39830000630

Reference yield:

: 32821-68-4,103957-83-1
3-ethyl-tetrahydro-pyran-2-one

: 88204-61-9
(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / diisobutylaluminium hydride / toluene / 0.75 h / -78 °C

2: 23 percent / dimethylformamide / 1. 2 h, 60 deg C 2. 90 min, 100 deg C 3. 1 h, 120 deg C

3: 99 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

4: 98 percent / diisobutylaluminium hydride / hexane; toluene / 0.25 h / -5 °C

5: 98 percent / diisopropylethylamine / CH₂Cl₂ / 2 h / Ambient temperature

6: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Ambient temperature

7: 100 percent / CrO₃-pyridine / CH₂Cl₂ / 0.42 h / Ambient temperature

8: 95 percent / CH₂Cl₂ / 7 h / Ambient temperature

9: 100 percent / toluene / 80 h / Heating

10: 65 percent / tetra-n-butylammonium bromide, conc.HCl / CH₂Cl₂ / 6 h / Ambient temperature

11: 29 percent / 2-hydroxypyridine / toluene / 6 h / 110 °C

With 1H-imidazole; 2-hydroxypyridin; hydrogenchloride; chromium trioxide-pyridine complex; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00193a014

Reference yield:

: 4-(Ethoxycarbonyl)hexan-1-ol

: 88204-61-9
(1S,3aR,4S,5R,7aS)-1-Ethyl-5-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Guidance literature:: Multi-step reaction with 12 steps

1: 34.0 g / p-TosOH / toluene / 1 h / Heating

2: 100 percent / diisobutylaluminium hydride / toluene / 0.75 h / -78 °C

3: 23 percent / dimethylformamide / 1. 2 h, 60 deg C 2. 90 min, 100 deg C 3. 1 h, 120 deg C

4: 99 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

5: 98 percent / diisobutylaluminium hydride / hexane; toluene / 0.25 h / -5 °C

6: 98 percent / diisopropylethylamine / CH₂Cl₂ / 2 h / Ambient temperature

7: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Ambient temperature

8: 100 percent / CrO₃-pyridine / CH₂Cl₂ / 0.42 h / Ambient temperature

9: 95 percent / CH₂Cl₂ / 7 h / Ambient temperature

10: 100 percent / toluene / 80 h / Heating

11: 65 percent / tetra-n-butylammonium bromide, conc.HCl / CH₂Cl₂ / 6 h / Ambient temperature

12: 29 percent / 2-hydroxypyridine / toluene / 6 h / 110 °C

With 1H-imidazole; 2-hydroxypyridin; hydrogenchloride; chromium trioxide-pyridine complex; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; diisobutylaluminium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00193a014