Sodium cyanoborohydride → n-[3-(4-Fluorophenyl)-propyl]-o-methyl-hydroxylamine
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C([BH3-])#N.[Na+]>>[F:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][NH:3][O:2][CH3:1])=[CH:12][CH:11]=1Participants
3
Procedure
Reduction of 3-(4-fluorophenyl)-propionaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography on silica gel and distillation in vacuo (75% yield): bp 70-75° C./0.7 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CHCl3) δ (ppm): 1.85 (2H, m, CH2), 2.68 (2H, t, J=7.9 Hz, CH2), 2.95 (2H, t, J=7.1 Hz, CH2), 3.56 (3H, s, OCH3), 5.58 (1H, broad, NH), 6.99 (2H, m, aromatics), 7.17 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 97-100° C. Anal. calcd for C10H14FNO—HCl: C, 54.67; H, 6.88; N, 6.38. Found: C, 54.72; H, 6.71; N, 6.42.
Sources & evidence
- ORD record
- ord-085b6c6b6671485e9baa861a924d4eca
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777440B2
Reaction notes
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