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Azeotropic elimination of water proved necessary for complete conversion of the starting material. (31) The configuration of each isomer was assigned from nOe experiments (see Supporting Information) and their ratio was determined from 1 H NMR spectra. (32) Clark (34) Treatment of 11 with catalytic amounts of various acids, with catalytic amounts of KCN, or excesses of hydroxylamine hydrochloride only led to recovery of the starting material, together with products of decomposition, pp.3466-789, 1978. ,
| doi: 10.1021/jo802255t TBAF on silica gel (15.40 g, 15.40 mmol) The reaction was stirred at room temperature during 14 h. The mixture was filtered, and the solid was washed with THF. The filtrate was concentrated under vacuum. Purification of the obtained residue by chromatography over silica gel (pentane/AcOEt CHCl 3 ), ) afforded pure nitrone 8 (2.32 g, 55%) as a yellow oil and oxime, 2009. ,
52 (dd, J ) 3.3, 9.6 Hz, 1H), p.59 ,
16-7.42 (m, 20H); 13 C NMR (75 MHz, CD 3 OD) ? ppm 59, dd, J ) 2.6, 10.2 Hz Hz, 1H), 4.49-4.69 (m, 5H), 4.75 (d, J ) 12.0 Hz, 1H), 4.84 (d, J ) 10.6 Hz, 1H); N, 2.68. (2R,3R,4R,5R)-2-(Hydroxymethyl)piperidine-1,3 To a stirred solution of hydroxylamine 12 (105 mg, 0.19 mmol) in CH 2 Cl 2, pp.7992-7995 ,
mL) was added, and then mixture was concentrated under vacuum This operation was repeated six times. The crude product was dissolved in H 2 O (4 mL) and stirred with DOWEX 1X8 (OH form ) until pH 6. After filtration, the filtrate was concentrated under vacuum to give 15 (31 mg, 91%) as a pale oil, pp.20-47 ,
175. 2 For reviews on the use of SmI 2 in organic synthesis, see: (a), HRMS (ESI) calcd for C 6 H 13 N 1 Na 1, pp.6859-99, 1980. ,
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Typical procedure: see ESI ?. 16 For reproducible results, co-evaporation of the starting nitrone several times with toluene, use of THF dried over molecular sieves, and thorough purge of the reaction media using Schlenk techniques were essential. Addition of proton sponge to the reaction mixtures did not improve the yields in alkylation products. 17 For a general review on the chemistry of nitrones see: (a) P. Merino, Science of Synthesis, Arkivoc Synlett Chem.?Eur. J. Angew. Chem., Int. Ed, vol.13, issue.18, pp.27-511, 2002. ,
Sandrine Py with Et 2 O. The organic phase was washed with brine, dried, filtered and concentrated. Purification of the residue by chromatography on silica gel (pentane/AcOEt: 3:1, 1:1, 0:1) afforded pure, p.86 ,
-3,4,5-Tris-Benzyloxy-2- Benzyloxymethyl-Piperidin-1-ol Colorless crystals, mp 78?80 °C, pp.9-10 ,
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