(NE)-N-(5-methylsulfinylpentylidene)hydroxylamine synthesis

5synthesis methods

Product Name:(NE)-N-(5-methylsulfinylpentylidene)hydroxylamine
CAS Number:1391062-46-6
Molecular formula:C6H13NO2S
Molecular Weight:163.2379

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(NE)-N-(5-methylsulfinylpentylidene)hydroxylamine

1391062-46-6
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$1320.00/250mg

Yield:1391062-46-6 91%

Reaction Conditions:

with sodium periodate in methanol;water; for 3 h;Cooling with ice;

Steps:

4.8.3. Synthesis of 8 from 7.

A solution of sodium metaperiodate (370 mg, 1.7 mmol) in water (5 mL) was added dropwise to a vigorously stirred ice-cold solution of 7 (240 mg, 1.6 mmol) in MeOH (15 mL). The reaction mixture was stirred for 3 h, then filtered at the pump and the filter cake was washed with MeOH. The combined filtrates were concentrated to ca. 10 mL and then extracted with CHCl3 (320 mL). The combined CHCl3 extracts were washed with water, dried, and concentrated under reduced pressure. Compound 8, as a mixture (R,S)s-sulfoxide isomers, was obtained as a colorless oil (240 mg, 91%) by flash column chromatography eluting with 90% DCM/MeOH. Rf=0.17 in 10% MeOH/DCM; IR(NaCl) υ max 3419, 2943, 2866, 2833, 1716, 1647, 1124, 1045,1018 cm^-¹; ¹H NMR (300 MHz, CDCl3) (300 K) δ 7.31 (t, 1H,J=6.3 Hz, 1H, CH]N), 6.61 (s, 1H, NOH), 2.71-2.54 (m, 2H, H5),2.51 (s, 3H, CH3SO), 2.35-2.13 (m, 2H, H2), 1.78-1.49 (m, 4H, H3 and H4); ¹³C NMR (75 MHz, CDCl3) (300 K)δ 150.3 (CH]N), 53.4,53.3 (C-5 isomers), 38.8 (CH3SO), 28.6 (C-2), 25.2, 24.8 (C-4 isomers), 21.9, 21.6 (C-3 isomers); HRMS (ESI) m/z for C6H14NO2S[MH]⁺, calcd 164.0740, found 164.0740.

References:

Vo, Quan V.;Trenerry, Craige;Rochfort, Simone;Hughes, Andrew B. [Tetrahedron,2013,vol. 69,# 41,p. 8731 - 8737]