(6S,8aR)-octahydro-6-indolizine

Base Information

• Chemical Name: (6S,8aR)-octahydro-6-indolizine
• CAS No.: 132256-87-2
• Molecular Formula: C₂₃H₂₈N₂O₂
• Molecular Weight: 364.488
• Mol file: 132256-87-2.mol

Synonyms:

Chemical Property of (6S,8aR)-octahydro-6-indolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,8aR)-octahydro-6-indolizine

There total 13 articles about (6S,8aR)-octahydro-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:

(S)-(+)-2-benzylamino glutaric acid (77539-18-5,73914-82-6) → (6S,8aR)-octahydro-6-indolizine (132256-87-2)

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: 1) t-BuLi / 1) pentane, Et₂O, -78 deg C, 2 h, 2) Et₂O, -78 deg C, 30 min

8: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

9: 60 percent / triphenylphosphine / tetrahydrofuran / 18 h / Ambient temperature

10: NH₄Cl / xylene / 4 h / Heating

11: AcOH, NaCNBH₃ / 18 h / Ambient temperature

With pyridine; dmap; borane-THF; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium cyanoborohydride; sodium hydrogencarbonate; ammonium chloride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; xylene;

DOI:10.1021/jo00040a045

Reference yield:

(S)-2--1,5-pentanediol (132316-97-3) → (6S,8aR)-octahydro-6-indolizine (132256-87-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / pyridine, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 48 h / Ambient temperature

3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

4: 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

5: 1) t-BuLi / 1) pentane, Et₂O, -78 deg C, 2 h, 2) Et₂O, -78 deg C, 30 min

6: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

7: 60 percent / triphenylphosphine / tetrahydrofuran / 18 h / Ambient temperature

8: NH₄Cl / xylene / 4 h / Heating

9: AcOH, NaCNBH₃ / 18 h / Ambient temperature

With pyridine; dmap; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium cyanoborohydride; ammonium chloride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; xylene;

DOI:10.1021/jo00040a045

Reference yield:

(S)-3,4,5,6-tetrahydro-5--2-cyclopropylpyridine (132256-85-0) → (6S,8aR)-octahydro-6-indolizine (132256-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄Cl / xylene / 4 h / Heating

2: AcOH, NaCNBH₃ / 18 h / Ambient temperature

With sodium cyanoborohydride; ammonium chloride; acetic acid; In xylene;

DOI:10.1021/jo00040a045

upstream raw materials:

Benzyl-(S)-2,3,5,6,7,8-hexahydro-indolizin-6-yl-carbamic acid benzyl ester

Benzyl-(2,3,5,6,7,8-hexahydro-indolizin-6-yl)-carbamic acid benzyl ester

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

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