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Volumn 2003, Issue 12, 2003, Pages 31-37

Tritylamine (triphenylmethylamine) in organic synthesis; II. The reactionof tritylamine with oxiranes - synthesis of N-trityl-β-aminoalcohols

Author keywords

aminoalcohol hydrochlorides; Ammonia equivalent; Epoxide ring opening; Oxirane; Tritylamine

Indexed keywords

1 (TRIPHENYLMETHYLAMINO)BUTAN 2 OL; 1 (TRIPHENYLMETHYLAMINO)PROPAN 2 OL; 1 AMINO 3 CHLORO 2 PROPANOL; 1 AMINOBUTAN 2 OL; 1 PHENYL 2 (TRIPHENYLMETHYLAMINO)ETHANOL; 2 (TRIPHENYLMETHYLAMINO)ETHANOL; 3 CHLORO 1 (TRIPHENYLMETHYLAMINO)PROPAN 2 OL; AMINE; AMINOALCOHOL; AMINOPROPANOL; ETHANOLAMINE; ETHYLENE OXIDE; HYDROCHLORIC ACID; PHENYLETHANOLAMINE; TRIPHENYLMETHYLAMINE; TRITANOL; UNCLASSIFIED DRUG;

EID: 3242702271     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (4)

References (49)
  • 7
    • 0016089632 scopus 로고
    • Tritylated 2-aminoethanol was used many times for introduction of 2-aminoethoxy groups into target molecules, mainly oligonucleotides. It was prepared in the reaction of trityl, or trityl like, chloride or bromide with 2-aminoethanol. For example see: a) Billimoria, J.D., Owen, J.S., Scott, G.H. Chem.Phys.Lipids 1974, 12, 327-43; Chem.Abstr. 1975, 83, 131086u;
    • (1974) Chem. Phys. Lipids , vol.12 , pp. 327-43
    • Billimoria, J.D.1    Owen, J.S.2    Scott, G.H.3
  • 8
    • 0016089632 scopus 로고
    • Tritylated 2-aminoethanol was used many times for introduction of 2-aminoethoxy groups into target molecules, mainly oligonucleotides. It was prepared in the reaction of trityl, or trityl like, chloride or bromide with 2-aminoethanol. For example see: a) Billimoria, J.D., Owen, J.S., Scott, G.H. Chem.Phys.Lipids 1974, 12, 327-43; Chem.Abstr. 1975, 83, 131086u;
    • (1975) Chem. Abstr. , vol.83
  • 19
    • 0026760304 scopus 로고
    • The reaction of tritylation of 2-aminoethanol was investigated in details by Butskus (ref. 4b) and Koermendy (Ref. 4d). There is only one example of tritylation of β-aminoalcohol other than 2-aminoethanol, described in: l) Bol, K.M., Liskamp, R.M.J. Tetrahedron Lett. 1991, 32, 5401-5404; l) Bol, K.M., Liskamp, R.M.J. Tetrahedron 1992, 48, 6425-6438.
    • (1992) Tetrahedron , vol.48 , pp. 6425-6438
    • Bol, K.M.1    Liskamp, R.M.J.2
  • 21
    • 0035854292 scopus 로고    scopus 로고
    • In fact, we have found only one paper in which the reaction of 4-chlorophenylglycidyl ether with tritylamine was described, see: Desai, R.C. J. Org. Chem. 2001, 66, 4939-4940.
    • (2001) J. Org. Chem. , vol.66 , pp. 4939-4940
    • Desai, R.C.1
  • 22
    • 3242735537 scopus 로고    scopus 로고
    • note
    • We have previously checked several solvents and found methanol to be superior over any other solvent. Isopropanol - a common solvent for epoxide ring opening reaction gave rather low yields of the desired product.
  • 43
    • 25944465098 scopus 로고
    • d) Protiva, M., Sustr, M., Borovička, M. Chem. Listy 1951, 45, 43-4; Chem. Abstr. 1951, 45, 9010e.
    • (1951) Chem. Abstr. , vol.45
  • 44
    • 3242738196 scopus 로고    scopus 로고
    • note
    • The crude product contains some polymeric fraction which could be removed by recrystallization from dioxane/water.
  • 45
    • 3242726639 scopus 로고    scopus 로고
    • note
    • Because its steric hindrance and high symmetry, the trityl group is dominating over the rest of molecule. This effect increases the melting points of all tritylated products and makes crystallization easy, so the trityl group is really the "crystal maker".
  • 46
    • 3242716604 scopus 로고    scopus 로고
    • note
    • The regioselectivity of the ring opening of propylene and butylene oxide is usually ignored in published papers. Authors believed that ring opening is giving always "beta" products.
  • 47
    • 3242669550 scopus 로고
    • It is worth to note that even before introduction of modern NMR instruments into organic labs, it was possible to determine the ratio of ring opening products just by recrystallization of the N-benzoyl derivatives of both aminoalcohols, for example, in the reaction of styrene oxide and ammonia. See: Castro, A.J., Brain, D.K., Fisher, H.D., Fuller, R.K. J. Org. Chem. 1954, 19, 1444.
    • (1954) J. Org. Chem. , vol.19 , pp. 1444
    • Castro, A.J.1    Brain, D.K.2    Fisher, H.D.3    Fuller, R.K.4
  • 48
    • 3242741760 scopus 로고    scopus 로고
    • note
    • The 1-phenyl-2-(triphenylmethylamino)ethanol was hydrolyzed 15 minutes in 2M hydrochloric acid, since concentrated hydrochloric acid gave also about 30% (molar) of the 2-chloro-2-phenylethyl(triphenylmethyl)amine which could be converted to the 2-amino-1-phenylethanol by increasing the time of hydrolysis. This chemistry, related to hydramine fission, is under investigation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.