(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

Base Information

Chemical Name:(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one
CAS No.:654061-24-2
Molecular Formula:C₁₆H₁₉NO₃
Molecular Weight:273.332
Hs Code.:

Synonyms:(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

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Chemical Property of (3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

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Technology Process of (3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

There total 3 articles about (3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]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: 44.0%

: 654061-22-0
(1R,4R,4aR,5aR)-5a-(2-methylallyl)-4-phenyltetrahydro-1,3-dioxa-4a-azacyclopropa[a]pentalen-5-one

: 654061-24-2
(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

: (3R,6S,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

Guidance literature:: (1R,4R,4aR,5aR)-5a-(2-methylallyl)-4-phenyltetrahydro-1,3-dioxa-4a-azacyclopropa[a]pentalen-5-one; With samarium diiodide; In tetrahydrofuran; isopropyl alcohol; for 1h;

In tetrahydrofuran; methanol; isopropyl alcohol; at -78 ℃; for 0.75h;
DOI:10.1055/s-2003-42426

Reference yield:

: (3R,7aR)-6-(2-Methyl-allyl)-3-phenyl-7-phenylselanyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 654061-24-2
(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 14.37 g / pyridine; aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

2.1: 92 percent / t-BuOOH; Triton B / tetrahydrofuran; toluene; methanol / 0 - 10 °C

3.1: SmI₂ / tetrahydrofuran; propan-2-ol / 1 h

3.2: 44 percent / tetrahydrofuran; propan-2-ol; methanol / 0.75 h / -78 °C

With pyridine; tert.-butylhydroperoxide; samarium diiodide; dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol; toluene;
DOI:10.1055/s-2003-42426

Reference yield:

: 654061-21-9
(3R,7aS)-6-(2-methylallyl)-3-phenyl-1,7a-dihydropyrrolo[1,2-c]oxazol-5-one

: 654061-24-2
(3R,6R,7aR,7S)-7-hydroxy-6-(2-methylallyl)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / t-BuOOH; Triton B / tetrahydrofuran; toluene; methanol / 0 - 10 °C

2.1: SmI₂ / tetrahydrofuran; propan-2-ol / 1 h

2.2: 44 percent / tetrahydrofuran; propan-2-ol; methanol / 0.75 h / -78 °C

With tert.-butylhydroperoxide; samarium diiodide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; isopropyl alcohol; toluene;
DOI:10.1055/s-2003-42426