Synthesis of two nuphar alkaloids by allenic hydroxylamine cyclisation

Synlett

Volumn , Issue 6, 2010, Pages 866-868

  Bates, Roderick W ^a   Lim, Chia Juan ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Alkaloids; Allenes; Cyclisation; Piperidines; Silver

Indexed keywords

ALKALOID DERIVATIVE; ALLENE DERIVATIVE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; SILVER;

AMINATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; NONHUMAN; NUPHAR; REDUCTION; STEREOCHEMISTRY;

EID: 77949901287     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219554     Document Type: Article

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36. NMR spectroscopic data for the trans isomer: 1H NMR (300 MHz, CDCl3): d = 1.08 (3 H, d, J = 6.8 Hz, CH3), 1.45 (9 H, s, t-Bu), 2.39 (1 H, m, CH), 3.41 (1 H, t, J = 8.3 Hz, CH2), 3.93 (1 H, t, J = 6.9 Hz, CH), 4.10 (1 H, t, J = 7.2 Hz,CH2), 5.13 (1 H, J = 10.1 Hz, =CH), 5.22 (1 H, J = 17.0 Hz, =CH), 5.76 (1 H, ddd, J = 7.2, 10.2, 16.8 Hz, =CH). 13C NMR (75 MHz, CDCl3): d = 14.5, 28.2, 43.8, 69.1, 75.0, 81.8, 115.8, 136.7, 157.0.
37. A suitable crystal was obtained from EtOAchexane. Empirical formula: C11H21NO3; formula weight: 215.29; temp: 173 (2) K; wavelength: 0.71073 ; crystal system: monoclinic; space group: P2 (1)/n; unit cell dimensions: a = 11.1651 (4) , a = 90, b = 11.2768 (4) , b = 115.343 (2), c = 11.1785 (5) , g = 90; volume: 1272.00(9) 3; Z: 4; density(calcd): 1.124 Mg/m3; absorption coefficient: 0.081 mm1; F(000): 472; crystal size: 0.30 0.30 0.14 mm3; q range for data collection: 2.1627.67; index ranges: 14h14, 12k14, 14 l 14; reflections collected: 12787; independent reflections: 2983 [R(int) = 0.0586]; completeness to q = 27.67: 99.9%; absorption correction; semi-empirical from equivalents; max. and min. transmission: 0.9888 and 0.9762; refinement method: full-matrix least-squares on F2; data/restraints/ parameters: 2983/0/144; goodness-of-fit on F2; 1.067; final R indices [I 2s(I)]R1 = 0.0652, wR2 = 0.1952; R indices (all data); R1 = 0.1041, wR2 = 0.2283; largest diff. peak and hole; 0.425 and 0.298 e 3. Details have been deposited with the Cambridge Crystallographic Data Centre, CCDC 764203, and may be obtained at http://www.ccdc.cam.ac.uk.
38. Diethyl methylphosphonate (8.71 g, 57.3 mmole) in THF (30 mL) and added via cannula to a solution of n-BuLi (48 mL of a 1.6 M solution in hexane, 71.6 mmol) in THF (50 mL) at 78 C. A solution of the Weinreb amide of 3-furoic acid (6.64 g, 47.7 mmol) in THF (20 mL) and added via cannula to the mixture. The mixture was stirred for 2 h. 2 M HCl was added to the mixture, and it was extracted twice with Et2O. The combined organic layers were dried (MgSO4), and concentrated to give phosphonate 8 as brown oil (15 g, 1.29 mmol, 72%), which was used without purification. 1H NMR (300 MHz, CDCl3): d = 1.30 (t, J = 7.05 Hz, 6 H, CH3), 3.39 (d, J = 22.7 Hz, 2 H, PCH2), 4.14 (m, 4 H, CH2), 6.80 (t, J = 1.2 Hz, 1 H, CH), 7.43 (s, 1 H, CH), 8.16 (s, 1 H, CH). 13C NMR (100 MHz, CDCl3): d = 16.2 (d, J = 5.7 Hz), 40.6 (d, J = 127.8 Hz), 62.7, 108.8, 127.7, 144.2, 149.1, 185.6 (d, J = 6.7 Hz).
39. NMR data for piperidine 12: 1H NMR (400 MHz, CDCl3): d = 0.89 (d, J = 6.4 Hz, 3 H), 1.101.30 (m, 3 H), 1.351.50 (1 H, m), 1.551.70 (1 H, m), 1.751.85 (2 H, m), 1.952.05 (1 H, m), 2.252.32 (1 H, m), 2.402.45 (2 H, m), 3.57 (m, 1 H), 3.65 (s, 3 H), 6.37 (s, 1 H), 7.33 (m, 2 H). 13C NMR (100 MHz, CDCl3): d = 18.4, 28.6, 30.2, 33.9, 34.1, 35.5, 51.5, 53.2, 62.3, 109.1, 129.5, 138.3, 142.7, 174.5.
40. Lactam 13 is also obtained if ester 12 is treated directly with methylmagnesium bromide.