(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

Base Information

Chemical Name:(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate
CAS No.:1417826-77-7
Molecular Formula:C₂₁H₁₉NO₅
Molecular Weight:365.386
Hs Code.:

Synonyms:(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

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Technology Process of (E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

There total 3 articles about (E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate 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%

: 2495-35-4,25036-21-9
benzylacrylate

: 1394957-71-1
(4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one

: 1417826-77-7
(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

Guidance literature:: With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 90 ℃; for 18h; Inert atmosphere;
DOI:10.1002/anie.201204991

Reference yield:

: 862095-79-2
indeno[2,1-b]-1,4-oxazin-3(2H)-one,4,4a,9,9a-tetrahydro-,(4aR,9aS)-

: 1417826-77-7
(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sulfuric acid; trifluoroacetic acid; N-Bromosuccinimide / 1.5 h / 0 - 5 °C / Inert atmosphere

1.2: Cooling with ice; Inert atmosphere

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C / Inert atmosphere

2.2: 72 h / 23 °C / Inert atmosphere; Darkness

3.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 18 h / 90 °C / Inert atmosphere

With N-Bromosuccinimide; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; In acetonitrile; 3.1: |Heck Reaction;
DOI:10.1002/anie.201204991

Reference yield:

: 1394957-70-0
(4aR,9aS)-6-bromo-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one

: 1417826-77-7
(E)-benzyl 3-((4aR,9aS)-4-hydroxy-3-oxo-2,3,4,4a,9,9a-hexahydroindeno[2,1-b][1,4]oxazin-6-yl)acrylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C / Inert atmosphere

1.2: 72 h / 23 °C / Inert atmosphere; Darkness

2.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 18 h / 90 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; 2.1: |Heck Reaction;
DOI:10.1002/anie.201204991