(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

Base Information

Chemical Name:(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one
CAS No.:630120-33-1
Molecular Formula:C₂₄H₃₆BrNO₃
Molecular Weight:466.459
Hs Code.:

Synonyms:(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

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Chemical Property of (3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

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Technology Process of (3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

There total 11 articles about (3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[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: 90.0%

: 630120-32-0
(3S,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyltetrahydropyrrolo[2,1-b]oxazol-5-one

: 74-88-4
methyl iodide

: 630120-33-1
(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

: (3S,6S,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

Guidance literature:: (3S,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyltetrahydropyrrolo[2,1-b]oxazol-5-one; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2003.08.089

Reference yield:

: 133129-29-0
2-bromo-6-methoxy-4-methylbenzaldehyde

: 630120-33-1
(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: (Me₃Si)2NK / toluene / 1 h

1.2: 76 percent / toluene / 10 h

2.1: 9-BBN / tetrahydrofuran / 10 h / 0 - 20 °C

2.2: 87 percent / aq. NaOH; aq. H₂O₂ / methanol / 2 h

3.1: Et₃N; MsCl / CH₂Cl₂ / 2 h

3.2: 92 percent / NaI / acetone / 24 h / Heating

4.1: BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 79 percent Turnov_. / HMPA / hexane; tetrahydrofuran / 37 h / -78 - 20 °C

5.1: n-BuLi; i-Pr₂NH / tetrahydrofuran / 1.5 h / -78 °C

5.2: 90 percent / HMPA / tetrahydrofuran / 13 h / -78 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; potassium hexamethylsilazane; methanesulfonyl chloride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.2: Wittig reaction;

Reference yield:

: 18432-37-6,60856-81-7
4-isobutyl-γ-butyrolactone

: 630120-33-1
(3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. H₂SO₄; Na₂Cr₂O₇; AcOH / 11 h

2.1: 75 percent / toluene / 15 h / Heating

3.1: BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 79 percent Turnov_. / HMPA / hexane; tetrahydrofuran / 37 h / -78 - 20 °C

4.1: n-BuLi; i-Pr₂NH / tetrahydrofuran / 1.5 h / -78 °C

4.2: 90 percent / HMPA / tetrahydrofuran / 13 h / -78 - 20 °C

With n-butyllithium; sodium dichromate; sulfuric acid; acetic acid; diisopropylamine; In tetrahydrofuran; hexane; toluene;