(1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine

Base Information

• Chemical Name: (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine
• CAS No.: 132317-05-6
• Molecular Formula: C₂₅H₃₀N₂O₄
• Molecular Weight: 422.524
• Mol file: 132317-05-6.mol

Synonyms:(1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine

Chemical Property of (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine

There total 16 articles about (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine 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: 90.0%

acetic anhydride (108-24-7) + (1S,6S,8aS)-octahydro-1-hydroxy-6-indolizine (132317-04-5) → (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine (132317-05-6)

Guidance literature:

With pyridine; at 23 ℃; for 18h;

DOI:10.1021/jo00006a002

Reference yield:

(S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6) → (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine (132317-05-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 71 percent / NaHCO₃ / H₂O / 3 h / Ambient temperature

2: 70 percent / BH₃*THF / tetrahydrofuran / 18 h / Ambient temperature

3: 88 percent / pyridine, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

4: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 48 h / Ambient temperature

5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

6: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

7: 3) 1 M HCl / 1) -78 deg C, 1 h, 2) r.t., 1 h, 3) 1 h

8: 67 percent / pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

9: 90 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

10: 1) H₂, 2) K₂CO₃ / 1) 10percent Pd-C / 1) 95percent EtOH, 22 h, 2) EtOH, reflux, 20 h

11: 90 percent / pyridine / 18 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; borane-THF; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00040a045

Reference yield:

(S)-4--5-azido-pentanal (132256-84-9) → (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine (132317-05-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 3) 1 M HCl / 1) -78 deg C, 1 h, 2) r.t., 1 h, 3) 1 h

2: 67 percent / pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

3: 90 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

4: 1) H₂, 2) K₂CO₃ / 1) 10percent Pd-C / 1) 95percent EtOH, 22 h, 2) EtOH, reflux, 20 h

5: 90 percent / pyridine / 18 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; hydrogen; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00040a045

upstream raw materials:

acetic anhydride

(1S,6S,8aS)-octahydro-1-hydroxy-6-indolizine

(S)-(+)-2-benzylamino glutaric acid

(S)-2--1,5-pentanediol

Downstream raw materials:

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

Refernces

• 1、 Pearson, William H.,Bergmeier, Stephen C.. "A Synthesis of (-)-Slaframine and (-)-1,8a-Diepislaframine". . p. 1976 - 1978. Retrieved 2007/10/02.