(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Base Information

Chemical Name:(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one
CAS No.:1413399-80-0
Molecular Formula:C₂₄H₂₇NO₃
Molecular Weight:377.483
Hs Code.:

Synonyms:(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

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Chemical Property of (3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

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Technology Process of (3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

There total 10 articles about (3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-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: 85.0%

: (S)-ethyl 2-((R)-(benzhydryloxy)((R)-oxiran-2-yl)methyl)piperidine-1-carboxylate

: 1826-67-1
vinyl magnesium bromide

: 1413399-80-0
(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: (S)-ethyl 2-((R)-(benzhydryloxy)((R)-oxiran-2-yl)methyl)piperidine-1-carboxylate; vinyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo4010553

Reference yield:

: 1413399-77-5
(S)-1-allyl-2-((R)-(benzhydryloxy)((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)piperidine

: 1413399-80-0
(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate / dichloromethane / 12 h / 20 °C / Reflux

2.1: Dowex 50 H⁺ / methanol / 12 h / Reflux

3.1: triethylamine; dmap; tert-butyldimethylsilyl chloride / dichloromethane / 12 h / 0 - 20 °C

3.2: 2 h / 0 - 20 °C

3.3: 1.5 h / 20 °C

4.1: copper(l) iodide / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C

With dmap; copper(l) iodide; sodium hydrogencarbonate; tert-butyldimethylsilyl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo4010553

Reference yield:

: 1413399-76-4
(R)-6-((R)-(benzhydryloxy)((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-methyl)tetrahydro-2H-pyran-2-one

: 1413399-80-0
(3R,4R,4aS)-3-allyl-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

2.1: triethylamine; dmap / dichloromethane / 2 h / 20 °C

3.1: methanol / 12 h / Reflux

4.1: sodium hydrogencarbonate / dichloromethane / 12 h / 20 °C / Reflux

5.1: Dowex 50 H⁺ / methanol / 12 h / Reflux

6.1: triethylamine; dmap; tert-butyldimethylsilyl chloride / dichloromethane / 12 h / 0 - 20 °C

6.2: 2 h / 0 - 20 °C

6.3: 1.5 h / 20 °C

7.1: copper(l) iodide / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.2: 2 h / 0 - 20 °C

With dmap; copper(l) iodide; lithium aluminium tetrahydride; sodium hydrogencarbonate; tert-butyldimethylsilyl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo4010553