Hydroxyamine hydrochloride → HCID 57893800, compound

HRID 1822009Notes

Reaction equation

HRID 1822009 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]=C(C3C=CC=CC=3)C3C=CC=CC=3)[N:16]=2)[CH2:10][C@@H:9]1[CH3:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].Cl.ON>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[N:16]=2)[CH2:10][C@@H:9]1[CH3:35])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57893610HCID 57893610, compound

Product 1

HCID 57893800HCID 57893800, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-[6-(benzhydrylidene-amino)-pyridin-2-yloxy]-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (preparation 62, 1.19 g) in methanol (30 mL), add sodium acetate (0.497 g), and hydroxyamine hydrochloride (0.316 g) and stir at room temperature. After 1 hr., partition between dichloromethane and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel column, eluting with dichloromethane-2M NH3 in methanol, gradient) to give the title compound (0.687 g). 1H NMR (CDCl3): 7.33 (t, 1H), 6.03 (m, 21), 5.25 (m, 1H), 4.33 (m, 3H), 3.87 (m, 1H), 3.25 (m, 1H), 1.91 (m, 3H), 1.73 (m, 1H), 1.46 (s, 9H), 1.27 (d, 3H).

Workup

  1. custom, partition between dichloromethane and saturated aqueous NaCl
  2. dry with materialdry over anhydrous sodium sulfate
  3. customevaporate
  4. custompurify on a silica gel column
  5. washeluting with dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-db2bcfb118ac46fa849db6cb50d2efb0
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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