(-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one

Base Information

• Chemical Name: (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one
• CAS No.: 158146-78-2
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.314
• Mol file: 158146-78-2.mol

Synonyms:(-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one

Chemical Property of (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one

There total 9 articles about (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-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: 95.0%

(2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole (316824-52-9) → (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one (158146-78-2)

Guidance literature:

With hexacarbonyl molybdenum; In water; acetonitrile; for 3h; Heating;

Reference yield:

(-)-(2S,3aS,3R,4R,6R)-3-Carbomethoxy-4-(benzoyloxy)-6-<(1S,2R)-2-phenyl-cyclohexyloxy>hexahydroisoxazolo<1,7-b> <1,2>oxazine-2-carboxylic acid methyl ester (158146-77-1) → (+)-(1R,6S,6aR,7S)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one + (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one (158146-78-2)

Guidance literature:

With hydrogen; W-2 Raney nickel; In methanol; for 14h; under 13445.8 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00098a027

Reference yield:

Benzoic acid (R)-1-hydroxy-pyrrolidin-3-yl ester → (-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one (158146-78-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HgO / CH₂Cl₂ / 4 h / 20 °C

2: 56 percent / benzene / 72 h / 20 °C

3: 95 percent / Mo(CO)6 / acetonitrile; H₂O / 3 h / Heating

With hexacarbonyl molybdenum; mercury(II) oxide; In dichloromethane; water; acetonitrile; benzene; 1: Oxidation / 2: Cycloaddition / 3: Ring cleavage;

upstream raw materials:

(-)-(2S,3aS,3R,4R,6R)-3-Carbomethoxy-4-(benzoyloxy)-6-<(1S,2R)-2-phenyl-cyclohexyloxy>hexahydroisoxazolo<1,7-b> <1,2>oxazine-2-carboxylic acid methyl ester

(2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

dimethyl cis-but-2-ene-1,4-dioate

benzoic acid