Hydroxylamine → HCID 178455123, compound

HRID 1093108Notes

Reaction equation

HRID 1093108 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][C:13]([O:18][CH2:19][CH2:20][OH:21])([C:16]#[N:17])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:22][OH:23]>C(O)C>[Si:1]([O:8][CH2:9][CH:10]1[CH2:11][CH2:12][C:13]([O:18][CH2:19][CH2:20][OH:21])([C:16](=[NH:17])[NH:22][OH:23])[CH2:14][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 57904860HCID 57904860, compound

Product 1

HCID 178455123HCID 178455123, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-((tert-butyldimethylsilyloxy)methyl)-1-(2-hydroxyethoxy)cyclohexane carbonitrile (3.44 g, 10.97 mmol) and 50% aq. hydroxylamine (0.725 g, 10.97 mmol) in ethanol (17 mL) was heated at 80° C. (oil bath temp) for 6 h. The mixture was concentrated to dryness in vacuo and the residual solid triturated with ethanol to obtain the title compound, 4-((tert-butyldimethylsilyloxy)methyl)-N-hydroxy-1-(2-hydroxyethoxy)cyclohexanecarboximidamide (3.30 g, 9.52 mmol, 87% yield) as a tan crystalline powder: HPLC: retention time=1.96 min (area percent=91%); LCMS: m/z 347 (M+H), 369 (M+Na); 1H NMR (500 MHz, CDCl3) δ ppm 0.02 (6H, s), 0.87 (9H, s),1.23 (1H, t, J=7.0 Hz), 1.25-1.34 (2H, m), 1.49-1.58 (2H, m), 1.57-1.63 (1H, m), 1.67-1.77 (2H, m), 2.05-2.16 (2H, m), 3.41-3.46 (4H, m), 3.69-3.72 (2H, m), 4.78 (2H, s), 7.95 (1H, brs); 13C NMR (126 MHz, CDCl3) δ ppm-5.22, 18.5, 25.0, 26.1, 32.0, 38.6, 62.1, 64.1, 66.9, 77.9, 154.7.

Workup

  1. concentrationThe mixture was concentrated to dryness in vacuo
  2. customthe residual solid triturated with ethanol

Sources & evidence

ORD record
ord-4344ab60d9ea4eb38e9cbd10c4a9ab76
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…