Hydroxyamine hydrochloride → HCID 58374065, compound

HRID 1948487Notes

Reaction equation

HRID 1948487 reaction equation
Br.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:23])[CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]2)=[CH:6][CH:5]=1)#[N:3].[CH3:24][Mg]Br.C(=O)(O)[O-].[Na+].Cl.[NH2:33][OH:34]>C1COCC1.C(OCC)(=O)C>[OH:23][C:10]([C:7]1[CH:6]=[CH:5][C:4](/[C:2](=[N:33]/[OH:34])/[NH2:3])=[CH:9][CH:8]=1)([CH3:24])[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 86656387HCID 86656387, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58374065HCID 58374065, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of (S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate, hydrobromide (100 mg, 0.262 mmol) in THF (2 mL) was added methylmagnesium bromide (0.350 mL, 1.049 mmol). After 1 hour, the reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated. The crude residue was dissolved in 2-propanol (10 mL). Sodium bicarbonate (88 mg, 1.049 mmol) and hydroxylamine hydrochloride (36.5 mg, 0.525 mmol) were added and the reaction was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried with MgSO4, filtered, and concentrated to yield 72 mg of (3S)-ethyl 1-(2-hydroxy-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)propyl)piperidine-3-carboxylate. MS (m+1)=350. HPLC Peak RT=0.11 minutes (Analytical Method B).

Workup

  1. customthe reaction was quenched with water
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude residue was dissolved in 2-propanol (10 mL)
  8. washwashed with saturated NaCl
  9. dry with materialThe organic layer was dried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-08e39a98c4934d34b065fa626623758e
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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