(2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile

Base Information

• Chemical Name: (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile
• CAS No.: 144478-69-3
• Molecular Formula: C₁₆H₁₈N₂O
• Molecular Weight: 254.332
• Mol file: 144478-69-3.mol

Synonyms:

Chemical Property of (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile

There total 13 articles about (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile 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:

(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one (65376-02-5) → (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile (144478-69-3,116174-37-9)

Guidance literature:

Multi-step reaction with 11 steps

1: CH₃ONa / toluene / 2 h / 100 °C

2: conc. H₂SO₄ / toluene; H₂O / 2.5 h / Heating

3: NH₄OH / toluene / 15 h / Ambient temperature

4: 1) NaOH, Br₂, 2) HCl / pH 1

5: H₂O / pH 7

7: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

8: 1 h / Ambient temperature

9: aq. HCl / methanol / 3 h / Ambient temperature; pH 1

10: Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

11: NaH / dimethylformamide / 4.5 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; sulfuric acid; water; bromine; sodium methylate; sodium hydride; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)61225-X

Reference yield:

dimethyl 1,2-cyclohexanedicarboxylate (4336-20-3) → (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile (144478-69-3,116174-37-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 35 °C / Pig Liver Esterase, pH 8.0, phosphate buffer

2: 77 percent / NaAlH₂(C₂H₅)2 / toluene / 3 h / Ambient temperature

3: CH₃ONa / toluene / 2 h / 100 °C

4: conc. H₂SO₄ / toluene; H₂O / 2.5 h / Heating

5: NH₄OH / toluene / 15 h / Ambient temperature

6: 1) NaOH, Br₂, 2) HCl / pH 1

7: H₂O / pH 7

9: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

10: 1 h / Ambient temperature

11: aq. HCl / methanol / 3 h / Ambient temperature; pH 1

12: Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

13: NaH / dimethylformamide / 4.5 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; sulfuric acid; water; bromine; sodium methylate; sodium hydride; triethylamine; sodium aluminum diethyl dihydride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)61225-X

Reference yield:

(1S,2S)-2-amino-cyclohexylmethanol (213993-31-8) → (2S,3aR,7aS)-1-Benzoyl-octahydro-indole-2-carbonitrile (144478-69-3,116174-37-9)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂O / pH 7

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 1 h / Ambient temperature

5: aq. HCl / methanol / 3 h / Ambient temperature; pH 1

6: Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

7: NaH / dimethylformamide / 4.5 h / Ambient temperature

With hydrogenchloride; water; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61225-X

upstream raw materials:

Methanesulfonic acid (1S,2S)-2-(benzoyl-cyanomethyl-amino)-cyclohexylmethyl ester

(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one

dimethyl 1,2-cyclohexanedicarboxylate

(1S,2S)-2-amino-cyclohexylmethanol