(-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine

Base Information

• Chemical Name: (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine
• CAS No.: 72362-29-9
• Molecular Formula: C₁₄H₁₉NOSe
• Molecular Weight: 296.271
• Mol file: 72362-29-9.mol

Synonyms:

Chemical Property of (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine

There total 7 articles about (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine 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:

(-)-(2S,4R)-N-formyl-4-formyloxyproline (73353-98-7) → (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine (72362-29-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / acetic anhydride / 10 h / 140 °C

2: 100 percent / conc. ethanolic ammonia / 16 h / Ambient temperature

3: 80 percent / hydrogen / 10percent Pd-C / acetic acid / 48 h / 15960 Torr / Ambient temperature

4: 90 percent / thionyl chloride / 5 h / Heating

5: 90 percent / hydrogen / Raney nickel / ethanol / 11400 Torr / Ambient temperature

6: 62 percent / i-Pr₂NH, n-BuLi

7: 61 percent / LiAlH₄

With lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; ammonia; hydrogen; diisopropylamine; palladium on activated charcoal; nickel; In ethanol; acetic anhydride; acetic acid;

DOI:10.1039/P19810000909

Reference yield:

ethyl (+)-2-(R)-2-hydroxy-2,3-dihydro-1H-pyrrolizine-7-carboxylate (73354-01-5) → (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine (72362-29-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / hydrogen / 10percent Pd-C / acetic acid / 48 h / 15960 Torr / Ambient temperature

2: 90 percent / thionyl chloride / 5 h / Heating

3: 90 percent / hydrogen / Raney nickel / ethanol / 11400 Torr / Ambient temperature

4: 62 percent / i-Pr₂NH, n-BuLi

5: 61 percent / LiAlH₄

With lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; hydrogen; diisopropylamine; palladium on activated charcoal; nickel; In ethanol; acetic acid;

DOI:10.1039/P19810000909

Reference yield:

ethyl (+)-6α-hydroxy-8β-pyrrolizidine-1α-carboxylate (73354-03-7) → (-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine (72362-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / thionyl chloride / 5 h / Heating

2: 90 percent / hydrogen / Raney nickel / ethanol / 11400 Torr / Ambient temperature

3: 62 percent / i-Pr₂NH, n-BuLi

4: 61 percent / LiAlH₄

With lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; hydrogen; diisopropylamine; nickel; In ethanol;

DOI:10.1039/P19810000909

upstream raw materials:

(-)-(2S,4R)-N-formyl-4-formyloxyproline

ethyl (+)-6α-hydroxy-8β-pyrrolizidine-1α-carboxylate

ethyl (+)-2-(R)-2-hydroxy-2,3-dihydro-1H-pyrrolizine-7-carboxylate

ethyl (+)-8β-pyrrolizidine-1α-carboxylate

Downstream raw materials:

(+)-supinidine