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Synlett
Volumn , Issue 1, 2008, Pages 0097-0099
A one-pot, solid-phase synthesis of secondary amines from reactive alkyl halides and an alkyl azide
Author keywords

Alkylation; Azides; Phosphinimine; Polymer supported triphenylphosphine; Secondary amines
Indexed keywords

HALIDE; TRIPHENYLPHOSPHINE;
EID: 38549111832     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990927     Document Type: Article
Times cited : (20)
References (31)
  • 18
    • 38549109845 scopus 로고    scopus 로고
    • Reagent purchased from Argonaut Technologies, P/N 800379.
    • Reagent purchased from Argonaut Technologies, P/N 800379.
  • 20
    • 38549152582 scopus 로고    scopus 로고
    • The compounds (Table 1, entries 1, 2, and 4) gave spectral data consistent with the assigned structures and in close agreement to the literature values. For recent examples, see: (a) Entry 1: Cho, B. T.; Kang, S. K. Tetrahedron 2005, 61, 5732.
    • The compounds (Table 1, entries 1, 2, and 4) gave spectral data consistent with the assigned structures and in close agreement to the literature values. For recent examples, see: (a) Entry 1: Cho, B. T.; Kang, S. K. Tetrahedron 2005, 61, 5732.
  • 21
    • 38549137102 scopus 로고    scopus 로고
    • Entry 2: Lu, Z.-H.; Bhongle, N.; Su, X.; Ribe, S.; Senenayake, C. H. Tetrahedron Lett. 2002, 43, 8620.
    • (b) Entry 2: Lu, Z.-H.; Bhongle, N.; Su, X.; Ribe, S.; Senenayake, C. H. Tetrahedron Lett. 2002, 43, 8620.
  • 22
    • 0000411838 scopus 로고    scopus 로고
    • Entry 4: Barluenga, J.; Canteli, R.-M.; Flórez, J. J. Org. Chem. 1994, 59, 602.
    • (c) Entry 4: Barluenga, J.; Canteli, R.-M.; Flórez, J. J. Org. Chem. 1994, 59, 602.
  • 23
    • 38549150573 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Secondary Amines 6 Anhyd THF (5 mL) was added to polymer-supported Ph3P9 (2.15 mmol/g, 200 mg, 0.43 mmol, The mixture was left to stand for 5 min, whereupon a solution of the azide (0.215 mmol) in anhyd THF (1 mL) was added. The suspension was agitated at r.t. for 4 h. To the mixture was added a solution of the alkylating reagent (0.645 mmol) in anhyd THF (500 μL, The mixture was agitated at r.t. for 16 h, filtered and the resin washed with anhyd THF (5 x 10 mL) and anhyds CH2Cl2 (5 x 10 mL, The resin was suspended in MeOH (2 mL) and transferred to a 4 mL screw-lock vial, and a solution of KOH (2% in MeOH, 2.15 mmol) was added. The suspension was agitated at 65°C for 4 h, cooled to r.t, filtered and the resin washed with CH2Cl 2 (4 x 3 mL) and MeOH 2 x 3 mL, The filtrate and washings were combined and concentrated to dryness. The crude product was partitioned bet
    • 4, filtered, and concentrated to give the amine. Yields and purities of isolated amines are shown in Table 1.
  • 24
    • 38549165507 scopus 로고    scopus 로고
    • Spectral Data for Table 1 Entry 3: 1H NMR (400 MHz, CDCl3, δ, 1.25 (s, 9 H, 1.55 (br s, 1 H, 3.78 (s, 2 H, 3.83 (s, 2H, 7.25-7.39 (m, 9 H, 13C NMR (100 MHz, CDCl 3, δ, 31.1, 34.6, 49.5, 49.8, 126.0, 127.3, 128.9, 129.3, 129.7, 129.9, 130.5, 152.5. MS (ES, m/z, 254.39 [H, M, HRMS (ES, m/z calcd for C18H 23N: 254.1903; found: 254.1904 [H, M, Entry 5: 1H NMR (400 MHz, CDCl3, δ, 1.32 (s, 9 H, 3.84 (s, 3 H, 4.34 (s, 2 H, 4.44 (br s, 1 H, 6.50 (d, J, 8.7 Hz, 2 H, 7.28 (d, J, 7.6 Hz, 2 H, 7.38 (d, J, 7.6 Hz, 2 H, 7.84 (d, J, 8.7 Hz, 2 H, 13C NMR (100 MHz, CDCl3, δ, 31.4, 34.6, 47.5, 51.5, 111.6, 118.6, 125.7, 127.3, 131.6, 135.3, 150.6, 151.8, 167.3. MS (ES, m/z, 298.23 [H, M, HRMS ES
    • +.
  • 26
    • 38549120529 scopus 로고    scopus 로고
    • Irgolic, K. J. In Houben-Weyl, 4th ed., E12b; Klamann, D., Ed.; Thieme: Stuttgart, 1990, 150.
    • (b) Irgolic, K. J. In Houben-Weyl, 4th ed., Vol. E12b; Klamann, D., Ed.; Thieme: Stuttgart, 1990, 150.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.