(1R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethanol

Base Information

• Chemical Name: (1R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethanol
• CAS No.: 245759-61-9
• Molecular Formula: C₂₅H₂₈N₂O₅
• Molecular Weight: 436.508
• Mol file: 245759-61-9.mol

Synonyms:

Chemical Property of (1R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethanol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethanol

There total 12 articles about (1R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethanol 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:

(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol (188690-82-6) → (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol (245759-61-9)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 2.5 h / 20 °C

2: dimethylsulfoxide / 87 h / 80 °C

3: neutral Al₂O₃ (activity III)

With aluminum oxide; potassium carbonate; In methanol; dimethyl sulfoxide; 1: Cyclization / 2: Addition / 3: Hydrolysis;

DOI:10.1016/S0957-4166(00)00238-X

Reference yield:

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene (37629-51-9) → (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol (245759-61-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / LiAlH₄ / diethyl ether / 2 h / Heating

2: Candida antarctica lipase B

3: 3M aq. KOH / Heating

4: dimethylsulfoxide / 87 h / 80 °C

5: neutral Al₂O₃ (activity III)

With Candida antarctica lipase B; aluminum oxide; potassium hydroxide; lithium aluminium tetrahydride; In diethyl ether; dimethyl sulfoxide; 1: Reduction / 2: Acetylation / 3: Hydrolysis / 4: Addition / 5: Hydrolysis;

DOI:10.1016/S0957-4166(00)00238-X

Reference yield:

4-benzyloxy-3-nitroacetophenone (14347-05-8) → (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol (245759-61-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / Br₂ / CHCl₃ / 25 °C

2: 87 percent / BH₃*THF / tetrahydrofuran / -20 °C

3: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C

4: K₂CO₃ / methanol / 2.5 h / 20 °C

5: dimethylsulfoxide / 87 h / 80 °C

6: neutral Al₂O₃ (activity III)

With aluminum oxide; borane-THF; lipase PS Celite-immobilized; bromine; potassium carbonate; In tetrahydrofuran; methanol; chloroform; dimethyl sulfoxide; 1: Bromination / 2: Reduction / 3: stereoselective / 4: Cyclization / 5: Addition / 6: Hydrolysis;

DOI:10.1016/S0957-4166(00)00238-X

upstream raw materials:

2-amino-1-(4-methyoxyphenyl)propane

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene

4-benzyloxy-3-nitroacetophenone

4-benzyloxy-3-nitrophenacyl bromide

Downstream raw materials:

N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide

(R,R)-formoterol

(R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol

Refernces