Hydroxylamine → HCID 59568782, compound

HRID 1643310Notes

Reaction equation

HRID 1643310 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH:6]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[O:7][CH3:8].CO.[NH2:19][OH:20].[C-]#N.[K+]>C1COCC1.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:6]([O:7][CH3:8])[CH2:5][CH2:4][C:3]([NH:19][OH:20])=[O:2])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 9032Potassium CyanideHCID 59568835HCID 59568835, compound

Product 1

HCID 59568782HCID 59568782, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-phenyl)-4-methoxy-butyric acid methyl ester (62.5 mg, 0.25 mmol) dissolved in 2 mL of THF, methanol, and 50 wt % NH2OH in H2O (2:2:1) mixture was added KCN (4.0 mg, 0.06) and the resulting mixture stirred for 3 days at room temperature. The reaction was quenched by the addition of 1M aqueous HCl (10 mL) and the resulting mixture extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×5 mL). The product was isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to give the title compound (34 mg) as colorless oil.

Workup

  1. customThe reaction was quenched by the addition of 1M aqueous HCl (10 mL)
  2. extractionthe resulting mixture extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with brine (2×5 mL)
  4. customThe product was isolated by flash column chromatography
  5. washeluting with 0% to 10% methanol/DCM

Sources & evidence

ORD record
ord-0d8e05dc0e5c4608a54a5ff38e841335
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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