ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate

Base Information

• Chemical Name: ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate
• CAS No.: 624736-74-9
• Molecular Formula: C₃₁H₃₉NO₇
• Molecular Weight: 537.653

Synonyms:ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate

Chemical Property of ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate

Chemical Property:

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Technology Process of ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate

There total 3 articles about ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate 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: 62.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + ethyl cyanoformate (623-49-4) + (6R)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(p-methoxyphenyl)-6H-1,2-oxazine (624736-70-5) → ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate (624736-74-9)

Guidance literature:

1,2-(methylenedioxy)-4-bromobenzene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

(6R)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(p-methoxyphenyl)-6H-1,2-oxazine; In tetrahydrofuran; pentane; at -78 ℃;

ethyl cyanoformate; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Further stages.;

DOI:10.1002/ejoc.200300234

Reference yield:

α-bromo-(p-methoxy)acetophenonoxime (71426-53-4) → ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate (624736-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium carbonate / CH₂Cl₂; various solvent(s) / 216 h / 20 °C

1.2: 44 percent / DBU / CH₂Cl₂; various solvent(s) / 16 h / 20 °C

2.1: 28 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 20 °C

3.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / -78 °C

3.3: 62 percent / tetrahydrofuran; pentane / 1 h / -78 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; sodium carbonate; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/ejoc.200300234

Reference yield:

6-ethoxy-3-(p-methoxyphenyl)-6H-1,2-oxazine (624736-67-0) → ethyl (6R)-5-(1,3-benzodioxol-5-yl)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-4-carboxylate (624736-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 28 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 20 °C

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: tetrahydrofuran; pentane / -78 °C

2.3: 62 percent / tetrahydrofuran; pentane / 1 h / -78 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/ejoc.200300234

upstream raw materials:

1,2-(methylenedioxy)-4-bromobenzene

ethyl cyanoformate

(6R)-6-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]-3-(p-methoxyphenyl)-6H-1,2-oxazine

α-bromo-(p-methoxy)acetophenonoxime

Downstream raw materials:

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

(2S,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

ethyl [2S,3R,4S]-2-(4-Methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

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