(S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine

Base Information

• Chemical Name: (S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine
• CAS No.: 157555-74-3
• Molecular Formula: C₁₀H₂₅NOSi
• Molecular Weight: 203.4
• DSSTox Substance ID: DTXSID30582041
• Wikidata: Q82473363
• Mol file: 157555-74-3.mol

Synonyms:(S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine;157555-74-3;(2S)-1-[tert-butyl(dimethyl)silyl]oxybutan-2-amine;1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-butanamine;SCHEMBL1587760;DTXSID30582041;(2S)-1-{[tert-Butyl(dimethyl)silyl]oxy}butan-2-amine

Chemical Property of (S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine

Chemical Property:

• Boiling Point: 215.9±13.0 °C(Predicted)
• PKA: 8.89±0.10(Predicted)
• PSA: 35.25000
• Density: 0.848±0.06 g/cm3(Predicted)
• LogP: 3.44580
• Solubility.: Chloroform, Dichloromethane, DMSO, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 203.170540955
• Heavy Atom Count: 13
• Complexity: 152

Purity/Quality:

97% ^*data from raw suppliers

(S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CO[Si](C)(C)C(C)(C)C)N
• Isomeric SMILES: CC[C@@H](CO[Si](C)(C)C(C)(C)C)N

Technology Process of (S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine

There total 6 articles about (S)-1-(tert-Butyldimethylsilyloxy)-2-butanamine 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: 95.0%

((S)-2-azidobutoxy)(tert-butyl)dimethylsilane (909567-50-6) → ((S)-2-aminobutoxy)(tert-butyl)dimethylsilane (157555-74-3)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; for 6h; under 760 Torr;

DOI:10.1016/j.tetasy.2006.06.011

Reference yield: 85.0%

(S)-2-aminobutan-1-ol (5856-62-2) + tert-butyldimethylsilyl chloride (18162-48-6) → ((S)-2-aminobutoxy)(tert-butyl)dimethylsilane (157555-74-3)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 25 ℃;

DOI:10.1016/j.tetasy.2006.06.011

Reference yield:

(R)-2-N-phenylaminooxy(tert-butyl)dimethylsilane (909567-48-2) → ((S)-2-aminobutoxy)(tert-butyl)dimethylsilane (157555-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 760 Torr

2: 95 percent / pyridine / 0 - 25 °C

3: 75 percent / sodium azide / dimethylformamide / 30 h / 60 °C

4: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 6 h / 760 Torr

With pyridine; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2006.06.011

upstream raw materials:

((S)-2-azidobutoxy)(tert-butyl)dimethylsilane

(S)-2-aminobutan-1-ol

tert-butyldimethylsilyl chloride

(R)-2-N-phenylaminooxy(tert-butyl)dimethylsilane

Downstream raw materials:

(S,S)-N¹,N²-bis(1-tert-butyldimethylsilyloxybutan-3-yl)oxamide

Refernces

• 1、 Barker, Timothy J.,Jarvo, Elizabeth R.. "Titanium-mediated amination of Grignard reagents using primary and secondary amines". supporting information; experimental part. p. 8325 - 8328. Retrieved 2011/10/31.
• 2、 Kotkar, Shriram P.,Sudalai, Arumugam. "Enantioselective synthesis of (S,S)-ethambutol using proline-catalyzed asymmetric α-aminooxylation and α-amination". . p. 1738 - 1742. Retrieved 2007/10/03.