N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester
• CAS No.: 218797-68-3
• Molecular Formula: C₁₅H₂₃NO₃
• Molecular Weight: 265.353
• DSSTox Substance ID: DTXSID001129512
• Nikkaji Number: J1.068.373D
• Mol file: 218797-68-3.mol

Synonyms:DTXSID001129512;Carbamic acid, [(1S,2S)-1-(hydroxymethyl)-2-phenylpropyl]-, 1,1-dimethylethyl ester;N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester;218797-68-3

Chemical Property of N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 265.16779360
• Heavy Atom Count: 19
• Complexity: 280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)C(CO)NC(=O)OC(C)(C)C
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)[C@@H](CO)NC(=O)OC(C)(C)C

Technology Process of N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester

There total 5 articles about N-[(alphaS,betaS)-alpha-(Hydroxymethyl)-beta-methylphenethyl]carbamic acid tert-butyl ester 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: 80.0%

(2S,3S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butoxycarbonyl)amino>-3-phenylbutane (218797-66-1) → (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3-phenylbutanol (218797-68-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo981140i

Reference yield:

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol (125414-45-1) → (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3-phenylbutanol (218797-68-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 83 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 23 °C

3: 75 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature

4: 1.) CuI / 1.) diethyl ether, 0 deg C, 2.) diethyl ether, 2 h

5: 80 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; dmap; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo981140i

Reference yield:

(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-<(tert-butoxycarbonyl)amino>-3-phenyl-2-propanol (153704-74-6) → (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3-phenylbutanol (218797-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 23 °C

2: 75 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature

3: 1.) CuI / 1.) diethyl ether, 0 deg C, 2.) diethyl ether, 2 h

4: 80 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / Ambient temperature

With dmap; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo981140i

upstream raw materials:

(2S,3S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butoxycarbonyl)amino>-3-phenylbutane

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol

(2R,3R)-1-<(tert-butyldimethylsilyl)oxy>-3-<(tert-butoxycarbonyl)amino>-3-phenyl-2-propanol

(2S,3R)-1-(tert-butoxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-phenylaziridine

Downstream raw materials:

(βS)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine