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

Base Information

• Chemical Name: (4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol
• CAS No.: 289046-86-2
• Molecular Formula: C₁₈H₂₅NO₂
• Molecular Weight: 287.402
• Mol file: 289046-86-2.mol

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

Chemical Property of (4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol

There total 1 articles about (4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol 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: 98.0%

Glyoxal (131543-46-9,107-22-2) + (1R,2S)-phenyl-2-(1-propyl-3-trimethylsilanylmethylbut-3-enylamino)ethanol (289046-84-0) → (4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol (289046-86-2)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 5h;

DOI:10.1021/jo0000271

Reference yield: 75.0%

(4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol (289046-86-2) → (4S,6R,9aS)-1-hydroxy-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-8-one (289046-87-3)

Guidance literature:

(4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol; With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; at 20 ℃; for 0.25h;

With sodium thiosulfate; In tetrahydrofuran; water; Further stages.;

DOI:10.1021/jo0000271

Reference yield:

(4S,6R,9aS)-8-methylene-4-phenyl-6-propyloctahydropyrido[2,1-c][1,4]oxazin-1-ol (289046-86-2) → (4S,6R,9aS)-4-phenyl-6-propylhexahydropyrido[2,1-c][1,4]oxazin-1-one (289046-92-0)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 75 percent / Na₂S₂O₃ / H₂O; tetrahydrofuran

2.1: 95 percent / BF₃*Et₂O / CHCl₃ / -10 - 20 °C

3.1: 77 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -60 - 20 °C

4.1: 45 percent / hydrogen; Raney nickel / methanol / 2 h

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; nickel; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 1.1: Oxidation / 1.2: Hydrolysis / 2.1: Cyclization / 3.1: Swern oxidation / 4.1: Hydrogenolysis;

DOI:10.1021/jo0000271

upstream raw materials:

Glyoxal

(1R,2S)-phenyl-2-(1-propyl-3-trimethylsilanylmethylbut-3-enylamino)ethanol

Downstream raw materials:

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

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

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

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