[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([N:19]1[CH2:25][CH2:24][CH2:23][C@H:20]1[CH2:21]O)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:15]([O:14][C:12]([N:19]1[CH2:25][CH2:24][CH2:23][C@H:20]1[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]To a stirred solution of methyl 4-hydroxybenzoate (1.96 g, 12.88 mmol), N-Boc-prolinol (2.59 g, 12.87 mmol) and PPh3 (4.06 g, 15.48 mmol) in THF (40 mL) was added DIAD (3.10 mL, 15.74 mmol). The resulting mixture was heated under reflux for 14 hr. The mixture was evaporated off in vacuo and the residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (6:1, v/v) as eluent to give 3.34 g (77%) methyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]benzoate as an oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 1.67 (d, J=9.3 Hz, 1 H), 1.87–2.03 (m, 3 H), 3.36–3.43 (m, 2H), 3.874.09 (m,l1H), 4.13–4.20 (m, 2 H, 6.94 (d, J=8.3 Hz, 2H), 7.98 (d, J=8.3 Hz, 2H).
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