Hydroxyamine hydrochloride → HCID 57893613, compound

HRID 1822000Notes

Reaction equation

HRID 1822000 reaction equation
C([O-])(=O)C.[Na+].Cl.ON.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=2)[CH2:18][C@@H:17]1[CH3:43])=[O:15])([CH3:12])([CH3:11])[CH3:10]>>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)[CH2:18][C@@H:17]1[CH3:43])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86607829HCID 86607829, compound

Product 1

HCID 57893613HCID 57893613, compound

Procedure

Add sodium acetate (0.309 g) and hydroxyamine hydrochloride (0.197 g) to 4-[3-(benzhydrylidene-amino)-phenoxy]-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (preparation 37) and stir at room temperature. After 1 hr., partition between ethyl acetate and saturated aqueous NaCl, dry over anhydrous sodium sulfate and evaporate. Purify on a silica gel column (35 g, solvent: dichloromethane-2M NH3 in methanol, gradient) to give the title compound (0.290 g). Mass spectrum (electrospray) m/z=251 (M-57+1), 207 (M-BOC+1); 1H NMR (CDCl3): 7.04 (t, 1H), 6.37 (d, 1H), 6.35 (d, 1H), 6.32 (t, 1H), 4.61 (m, 1H), 4.33 (m, 3H), 3.86 (m, 1H), 3.25 (m, 1H), 1.93 (m, 2H), 1.86 (m, 1H), 1.70 (m, 1H), 1.46 (s, 9H), 1.29 (d, J=7.1 Hz, 3H).

Workup

  1. custom, partition between ethyl acetate and saturated aqueous NaCl
  2. dry with materialdry over anhydrous sodium sulfate
  3. customevaporate
  4. customPurify on a silica gel column (35 g, solvent: dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-065d81e356824b72938af19522ff5e76
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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