(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

Base Information

Chemical Name:(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one
CAS No.:183612-77-3
Molecular Formula:C₂₈H₃₅BrN₂O₃
Molecular Weight:527.501
Hs Code.:

Synonyms:(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

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Chemical Property of (3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

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Technology Process of (3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

There total 7 articles about (3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-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: 84.0%

: {benzyl[(trimethylsilyl)methyl]amino}methanol

: 183612-76-2
(3S,7aR)-6-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-7a-methyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one

: 183612-77-3
(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

: (3S,5aS,8aR,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

Guidance literature:: With trifluoroacetic acid; In dichloromethane; benzene; for 36h; Yields of byproduct given;
DOI:10.1021/ja961903o

Reference yield:

: 5020-41-7
2-(3-methoxyphenyl)-ethanol

: 183612-77-3
(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

Guidance literature:: Multi-step reaction with 6 steps

1: 96.7 percent / PPh₃, I₂, imidazole / CH₂Cl₂ / 3 h / Ambient temperature

2: 95 percent / Br₂ / CH₂Cl₂ / 2 h / -10 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, 0 deg C, 6 h

4: KH / tetrahydrofuran / 1.5 h / 25 °C

5: 30percent aq. H₂O₂ / 12 h / Ambient temperature

6: 84 percent / trifluoroacetic acid / benzene; CH₂Cl₂ / 36 h

With 1H-imidazole; dihydrogen peroxide; bromine; iodine; potassium hydride; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja961903o

Reference yield:

: 25226-97-5
3-methoxyphenethyl iodide

: 183612-77-3
(3S,5aR,8aS,8bR)-7-Benzyl-5a-[2-(2-bromo-5-methoxy-phenyl)-ethyl]-3-isopropyl-8b-methyl-octahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]oxazol-5-one

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / Br₂ / CH₂Cl₂ / 2 h / -10 °C

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, 0 deg C, 6 h

3: KH / tetrahydrofuran / 1.5 h / 25 °C

4: 30percent aq. H₂O₂ / 12 h / Ambient temperature

5: 84 percent / trifluoroacetic acid / benzene; CH₂Cl₂ / 36 h

With dihydrogen peroxide; bromine; potassium hydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja961903o