[(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate

Base Information

• Chemical Name: [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate
• CAS No.: 1440869-82-8
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304
• Mol file: 1440869-82-8.mol

Synonyms:

Chemical Property of [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate

There total 12 articles about [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate 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:

C8H13NO3 + benzoic acid anhydride (93-97-0) → [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate (1440869-82-8)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201207800

Reference yield:

[(2S,4S,5S)-5-allyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol → [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate (1440869-82-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 2-iodoxybenzoic acid / dichloromethane / 3 h / Inert atmosphere; Molecular sieve; Reflux

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

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

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

5: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

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

7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

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

9: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

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

11: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

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

13: triethylamine / acetonitrile / 1 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; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; 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; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 8: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

Reference yield:

(E)-methyl 3-[(2S,4R,5S)-5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acrylate → [(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate (1440869-82-8)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

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

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

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

6: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 2 h / 20 °C / Inert atmosphere

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

8: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 1 h / 20 °C / Inert atmosphere

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

10: triethylamine / acetonitrile / 1 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; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; 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; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 5: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

upstream raw materials:

benzoic acid anhydride

(2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one

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

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

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