(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

Base Information

Chemical Name:(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester
CAS No.:80361-14-4
Molecular Formula:C₂₁H₂₇NO₅
Molecular Weight:373.449
Hs Code.:

Synonyms:(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

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Chemical Property of (3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

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Technology Process of (3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

There total 17 articles about (3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester 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: 65.0%

: 80361-12-2
(3aS,4S,5S,7S,7aR)-2-Benzoyl-1-benzyl-4-ethoxycarbonyloxymethyl-5-hydroxy-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

: 80361-14-4
(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/jo00347a034

Reference yield:

: 14293-06-2
5-(phenylmethyl)pyrrolidin-2-one

: 80361-14-4
(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 77 percent / sodium hydride / tetrahydrofuran / 0 °C

2: LDA, hexamethylphosphoramide / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

3: 1.) LDA, HMPA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

4: 64 percent / 30percent H₂O₂, glacial acetic acid / H₂O; tetrahydrofuran / 2 h / 0 °C

5: 26 mg / benzene-d6 / 1 h / 130 °C

6: NaIO₄ / methanol; H₂O / 48 h / 23 °C

7: triethyl phosphite / ethanol / 24 h / 23 °C

8: 65 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene-d6; water;
DOI:10.1021/jo00347a034

Reference yield:

: 90741-72-3
rac-1-benzoyl-5-benzylpyrrolidin-2-one

: 80361-14-4
(3aR,4R,5R,7R,7aS)-1-Benzyl-5-hydroxy-4-hydroxymethyl-7-methyl-6-methylene-3-oxo-octahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: LDA, hexamethylphosphoramide / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

3: 64 percent / 30percent H₂O₂, glacial acetic acid / H₂O; tetrahydrofuran / 2 h / 0 °C

4: 26 mg / benzene-d6 / 1 h / 130 °C

5: NaIO₄ / methanol; H₂O / 48 h / 23 °C

6: triethyl phosphite / ethanol / 24 h / 23 °C

7: 65 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene-d6; water;
DOI:10.1021/jo00347a034