328969-74-0

Basic information

• Product Name: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol
• Synonyms: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol
• CAS NO: 328969-74-0
• Molecular Weight: 329.439
• Mol File: 328969-74-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol(328969-74-0)
• EPA Substance Registry System: rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol(328969-74-0)

Safety Data

• Hazardous Substances Data: 328969-74-0(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 111749-17-8 2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol 
• 768-90-1 1-Adamantyl bromide 
• 100926-39-4 Ethyl N-acetyl-α-amino-(1-adamantyl)acetate 
• 59768-71-7 2-(adamantan-1-yl)-2-aminoacetic acid 
• 30504-23-5 ethyl 2-(adamantan-1-yl)-3-oxobutanoate 

Downstream Products

• 328969-77-3 (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 

Relevant articles and documents

Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: A combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1.