Ammonium Chloride → 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23](O)=[O:24])=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][OH:24])=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
BH3-THF complex (1.0 M sol., 0.13 mL, 0.13 mmol) was added to a solution of [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetic acid (40.0 mg, 0.11 mmol) in THF (5 mL) under N2 atmosphere and stirred overnight. The reaction mixture was treated with saturated aqueous NH4Cl (1 mL) and extracted with AcOEt (20 mL), The organic layer was washed with saturated aqueous NaCl (5 mL), dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography (25% AcOEt-Petroleum ether) afforded 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol (21.2 mg, 53%) as a dark red solid. M.p. 128-130° C.; 1H NMR (CDCl3, 500 MHz) δ 8.24 (d, 9.0, 1H), 7.88 (d, 8.0, 1H), 7.66 (t, 7.5, 1H), 7.60 (t, 7.5, 1H), 7.45 (d, 7.5, 2H), 7.41 (t, 7.5, 2H), 7.35 (t, 7.5, 1H), 6.92 (s, 1H), 4.87 (brs, 1H), 4.50 (d, 5.0, 2H), 4.05 (t, 8.5, 2H), 3.40 (t, 7.0, 2H), 1.84 (brs, 1H); IR (neat) 3406, 2936, 2892, 1594, 1519, 1435, 1342, 1124, 1036, 912, 823, 752, 699 cm−1. FABMS (NBA) m/z 322 (M−CO2+), ESMS m/z 323 (M−CO2+H+), 645 ((M−CO2)×2+H+).