(3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one

Base Information

• Chemical Name: (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one
• CAS No.: 612820-34-5
• Molecular Formula: C₁₆H₂₀N₄O₂
• Molecular Weight: 300.36
• Mol file: 612820-34-5.mol

Synonyms:(3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one

Chemical Property of (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one

There total 18 articles about (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one 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%

(3S,6R,9S)-3-(tert-butyldiphenylsilanyloxymethyl)-6-azido-6-benzylhexahydroindolizin-5-one (612820-32-3) → (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one (612820-34-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.25h;

Reference yield:

<2S-trans-(Z)>-5-Propenyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester (161424-44-8) → (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one (612820-34-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

2.1: 3.39 g / EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

3.1: 96 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 4 h / Heating

4.1: 94 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h

5.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

6.1: sodium borohydride / methanol / 2 h / 20 °C

7.1: 772 mg / imidazole / dimethylformamide / 16 h / 20 °C

8.1: 96 percent / hydrogen / Pd/C / ethyl acetate / 16 h / 20 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

9.2: 67 percent / tetrahydrofuran; pentane / 1 h / -78 °C

10.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / -78 °C

10.2: 15 percent / trisyl azide / tetrahydrofuran; pentane / 6 h / -78 °C

11.1: 90 percent / TBAF / tetrahydrofuran / 1.25 h

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; Grubbs catalyst first generation; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane; 3.1: Grubbs olefin metathesis reaction;

Reference yield:

(2S,5S)-((Z)-5-Propenyl)-pyrrolidine-2-carboxylic acid methyl ester → (3S,6R,9S)-3-hydroxymethyl-6-azido-6-benzylhexahydroindolizin-5-one (612820-34-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 3.39 g / EDC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h

2.1: 96 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 4 h / Heating

3.1: 94 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h

4.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

5.1: sodium borohydride / methanol / 2 h / 20 °C

6.1: 772 mg / imidazole / dimethylformamide / 16 h / 20 °C

7.1: 96 percent / hydrogen / Pd/C / ethyl acetate / 16 h / 20 °C

8.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

8.2: 67 percent / tetrahydrofuran; pentane / 1 h / -78 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / -78 °C

9.2: 15 percent / trisyl azide / tetrahydrofuran; pentane / 6 h / -78 °C

10.1: 90 percent / TBAF / tetrahydrofuran / 1.25 h

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; Grubbs catalyst first generation; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane; 2.1: Grubbs olefin metathesis reaction;

upstream raw materials:

(3S,6R,9S)-3-(tert-butyldiphenylsilanyloxymethyl)-6-azido-6-benzylhexahydroindolizin-5-one

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

(5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine

<2S-trans-(Z)>-5-Propenyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester

Downstream raw materials:

(3S,6R,9S)-6-azido-6-benzyl-5-oxooctahydroindolizine-3-carboxylic acid 4-N-Cbz-carbamimidoylbenzylamide