Reaction Steps
To a magnetically stirred solution of 2-allyl-4-benzyl-8-iodo-2,3,4,5-tetrahydro-1H-5-oxa-2-benzazepin-1-one (0.9234 grams, 2.2 mmol) in 4 mL THF at room temperature under an atmosphere of nitrogen was added 6.0 mL of a 0.5M solution of 9-borabicylo[3.3.1]nonane in THF (3 mmol) and the mixture stirred for 1 hour. The reaction was quenched with 6 mL of a solution of 2 grams of sodium hydroxide and 22 mL of a 1:1 mixture of ethanol and water. To the resulting solution was added 7 mL of a 30% solution hydrogen peroxide in water. After 30 minutes the mixture was partitioned between diethyl ether and water. The organic layer was washed with 10% citric acid and brine, dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography (SiO2, using 1:5 ethyl acetate/methylene chloride as the eluting solvent, Rf (product)=0.22) to yield 0.74 grams (77%) of 2-(3-hydroxypropyl)-4-benzyl-8-iodo-2,3,4,5-tetrahydro-1H-5-oxa-2-benzazepin-1-one. 1H NMR (CDCl3, dTMS) 8.08 (1H, d, 4JHH =2 Hz, C9-H), 7.71 (1H, dd, 4JHH =2 Hz, 3JHH =8 Hz, C7-H), 7.4 -7.2 (5H, m, C6H5), 6.78 (1H, d, 3JHH =8 Hz, C6-H), 4.64 (1H, m, ArOCH), 3.70 (2H, m, CH2OH), 3.58 (2H, bt, 3JHH =5 Hz, NCH2CH2), 3.39 (1H, dd, 2JHH =15 Hz, 3JHH =8 Hz, C3-H), 3.24 (1H, dd, 2JHH =15 Hz, 3JHH =3 Hz, C3-H), 3.1 (1H, dd, 2JHH =14 Hz, 3JHH =7 Hz, CHHPh), 2.76 (1H, dd, 2JHH =14 Hz, 3JHH =7 Hz, CHHPh), 1.68 (2H, m, CH2CH2OH). 13C NMR (CDCl3) 168.3, 152.6, 141.6, 139.4, 136.2, 132.1, 131.9, 129.2, 129.0, 128.8, 128.4, 127.0, 124.7, 86.8, 85.7, 58.0, 49.9, 44.5, 38.8, 30.3. IR (NaCl, cm-1) 3422 (b), 1636, 1463, 1436, 1217, 1064.
