[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:18]=[N+]=[N-])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH2:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Dissolved 1-benzyloxycarbonyl-3-azidomethylpiperidine (1.27 g, 4.63 mmol, 1 eq) in THF (50 mL). Added water (10 mL). Added triphenylphosphine (1.5 g, 5.79 mmol, 1.25 eq) and let stir overnight. Removed solvent under reduced pressure and diluted the residue with 80 mL 1N HCl. Extracted the solution 3× with ethyl acetate to remove neutral organics. Basified the aqueous layer with 5N NaOH and extracted 3× with ethyl acetate. Combined the organic layers, dried over anhydrous Na2SO4, filtered and concentrated giving 903 mg of the desired amine.
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