(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

Base Information

Chemical Name:(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one
CAS No.:289046-94-2
Molecular Formula:C₁₇H₂₃NO₃
Molecular Weight:289.375
Hs Code.:

Synonyms:(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

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Chemical Property of (4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

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Technology Process of (4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

There total 4 articles about (4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-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: 54.0%

: 289046-93-1
(4S,6R,9aS)-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazine-1,8-dione

: 289046-94-2
(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

Guidance literature:: With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 ℃; for 1.33333h;
DOI:10.1021/jo0000271

Reference yield:

: 289046-87-3
(4S,6R,9aS)-1-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-8-one

: 289046-94-2
(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -60 - 20 °C

2: 54 percent / K-Selectride / tetrahydrofuran / 1.33 h / -78 °C

With oxalyl dichloride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Reduction;
DOI:10.1021/jo0000271

Reference yield:

: 289046-86-2
(4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol

: 289046-94-2
(4S,6R,8S,9aS)-8-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: osmium tetraoxide; sodium periodate / H₂O; tetrahydrofuran / 0.25 h / 20 °C

1.2: 75 percent / Na₂S₂O₃ / H₂O; tetrahydrofuran

2.1: 90 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -60 - 20 °C

3.1: 54 percent / K-Selectride / tetrahydrofuran / 1.33 h / -78 °C

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1.1: Oxidation / 1.2: Hydrolysis / 2.1: Swern oxidation / 3.1: Reduction;
DOI:10.1021/jo0000271