Sodium cyanoborohydride → HCID 21947412, compound

HRID 1836485Notes

Reaction equation

[CH2:1]([O:5][N:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH:2]([CH3:4])[CH3:3].C([BH3-])#N.[Na+]>>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][NH:6][O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 5003444Sodium cyanoborohydride

HCID 73855557HCID 73855557, compound

Product 1

HCID 21947412HCID 21947412, compoundYield 65%

Procedure

Reduction of 4-fluorobenzaldehyde O-isobutyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography (65% yield). 1HNMR 400 MHz (C6D6) δ (ppm): 0.87 (6H, d, J=6.75 Hz, CH3), 1.88 (1H, m, CH), 3.46 (2H, d, J=6.41 Hz, OCH2), 4.05 (2H, s, NCH2), 7.04 (2H, m, aromatics), 7.37 (2H, m, aromatics). Anal. calcd for C11H16FNO: C, 66.98; H, 8.17; N, 7.10. Found: C, 66.88; H, 7.97; N, 7.32.

Sources & evidence

ORD record: ord-f57972d2655d41a49dd5bfb83ad4768b
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

Loading…