(7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one

Base Information

• Chemical Name: (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one
• CAS No.: 1440870-60-9
• Molecular Formula: C₂₀H₂₉NO₆
• Molecular Weight: 379.453
• Mol file: 1440870-60-9.mol

Synonyms:(7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one

Chemical Property of (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one

There total 17 articles about (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-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: 88.0%

[(1S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-5-oxohexahydro-1H-pyrrolizin-1-yl]methylbenzoate → (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one (1440870-60-9)

Guidance literature:

With lithium hydroxide monohydrate; water; In methanol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201207800

Reference yield:

[(2S,4S,5S)-5-allyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol → (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one (1440870-60-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 2-iodoxybenzoic acid / dichloromethane / 3 h / Inert atmosphere; Molecular sieve; Reflux

2.1: ozone / dichloromethane; methanol / 0.17 h / -78 °C / Inert atmosphere

3.1: sodium tetrahydroborate / dichloromethane; methanol / 2 h / -78 - 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate; nickel dichloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

6.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 20 °C / Inert atmosphere

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

9.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

10.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

11.1: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

13.1: triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

14.1: (+)-10-camphorsulfonic acid / toluene / 0.67 h / 20 °C / Inert atmosphere

14.2: Inert atmosphere

15.1: acetic anhydride / pyridine / 0.67 h / 20 °C / Inert atmosphere

16.1: water; lithium hydroxide monohydrate / methanol / 2 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; tetra-n-propylammonium perruthenate.; lithium hydroxide monohydrate; 2-iodoxybenzoic acid; tributylphosphine; 10 wt% Pd(OH)2 on carbon; (+)-10-camphorsulfonic acid; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 8.1: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

Reference yield:

(E)-methyl 3-[(2S,4R,5S)-5-allyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acrylate → (7S,7aS)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one (1440870-60-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: ozone / dichloromethane; methanol / 0.17 h / -78 °C / Inert atmosphere

2.1: sodium tetrahydroborate / dichloromethane; methanol / 2 h / -78 - 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate; nickel dichloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 20 °C / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

8.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

9.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

10.1: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

12.1: triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

13.1: (+)-10-camphorsulfonic acid / toluene / 0.67 h / 20 °C / Inert atmosphere

13.2: Inert atmosphere

14.1: acetic anhydride / pyridine / 0.67 h / 20 °C / Inert atmosphere

15.1: water; lithium hydroxide monohydrate / methanol / 2 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; tetra-n-propylammonium perruthenate.; lithium hydroxide monohydrate; tributylphosphine; 10 wt% Pd(OH)2 on carbon; (+)-10-camphorsulfonic acid; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 7.1: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

upstream raw materials:

(5R,6S)-5-hydroxy-6-(hydroxymethyl)azocan-2-one

(5R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-5-hydroxyazocan-2-one

(7S)-7-[(tert-butyldiphenylsilyloxy)methyl]-7a-hydroxytetrahydro-1H-pyrrolizin-3(2H)-one

3-(3,4-dimethoxybenzyl)oxypropan-1-ol

Downstream raw materials:

(7S,7aS)-7-(tert-butyldimethylsilyloxymethyl)-7a-[3-(3,4-dimethoxybenzyloxy)propoxy]-tetrahydro-1H-pyrrolizin-3(2H)-one

(7S,7aS)-7-(((tert-butyldimethylsilyl)oxy)methyl)-7a-(3-((3,4-dimethoxybenzyl)oxy)propoxy)-2-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)tetrahydro-1Hpyrrolizin-3(2H)-one

(2R,7S,7aS)-7-(((tert-butyldimethylsilyl)oxy)methyl)-7a-(3-((3,4-dimethoxybenzyl)oxy)propoxy)-2-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-2-(phenylthio)tetrahydro-1H-pyrrolizin-3(2H)-one

(2R,7S,7aS)-7a-(3-((3,4-dimethoxybenzyl)oxy)propoxy)-7-(hydroxymethyl)-2-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-2-(phenylthio)tetrahydro-1H-pyrrolizin-3(2H)-one