rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol

Base Information

• Chemical Name: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol
• CAS No.: 328969-74-0
• Molecular Formula: C₂₀H₂₇NO₃
• Molecular Weight: 329.439
• Mol file: 328969-74-0.mol

Synonyms:rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol

Chemical Property of rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol

There total 6 articles about rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 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: 72.0%

benzyl chloroformate (501-53-1,94274-21-2) + 2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol (111749-17-8) → rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol (328969-74-0)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 18h;

DOI:10.1016/S0957-4166(00)00428-6

Reference yield:

1-Adamantyl bromide (768-90-1) → rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol (328969-74-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / cobalt(II) chloride bis-triphenylphosphine; lanthanum(III) bromide hexahydrate / CHCl₃ / 44 h / 140 °C

2: 70 percent / methanesulfonic acid; sodium azide / 1,2-dimethoxy-ethane / -30 - 20 °C

3: 85 percent / 7 M hydrochloric acid / 12 h / Heating

4: 76 percent / sodium borohydride; I₂ / tetrahydrofuran / 0 - 20 °C

5: 72 percent / sodium carbonate / tetrahydrofuran; H₂O / 18 h / 0 - 20 °C

With hydrogenchloride; sodium tetrahydroborate; bis(triphenylphosphine)dichlorocobalt(II); sodium azide; methanesulfonic acid; lanthanum bromide; iodine; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; chloroform; water; 2: Schmidt rearrangement;

DOI:10.1016/S0957-4166(00)00428-6

Reference yield:

2-(adamantan-1-yl)-2-aminoacetic acid (59768-71-7,60256-21-5,95853-35-3,100926-41-8) → rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol (328969-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / sodium borohydride; I₂ / tetrahydrofuran / 16 h / Heating

2: 72 percent / sodium carbonate / tetrahydrofuran; H₂O / 18 h / 0 - 20 °C

With sodium tetrahydroborate; iodine; sodium carbonate; In tetrahydrofuran; water;

DOI:10.1016/S0957-4166(00)00428-6

upstream raw materials:

benzyl chloroformate

2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol

1-Adamantyl bromide

2-(adamantan-1-yl)-2-aminoacetic acid

Downstream raw materials:

(S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol

Refernces