Hydroxylamine → HCID 59568849, compound

HRID 1643303Notes

Reaction equation

HRID 1643303 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH:6]([O:14][CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].C1COCC1.[NH2:22][OH:23].[C-]#N.[K+]>O.CO>[OH:23][NH:22][C:3](=[O:2])[CH2:4][CH2:5][CH:6]([O:14][CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 9032Potassium CyanideHCID 59568776HCID 59568776, compound

Product 1

HCID 59568849HCID 59568849, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution prepared by dissolving 4-methoxy-4-o-tolyl-butyric acid methyl ester (230.0 mg, 1.03 mmol) into 3 mL of a mixture of THF, methanol, and 50 wt % NH2OH in H2O (2:2:1) was added KCN (6.0 mg, 0.03 mmol). The reaction mixture was stirred for 3 days at room temperature and then quenched by the addition of 10 mL of 1M aqueous HCl. The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with brine (2×10 mL). The product was isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to afford 184 mg of the title compound as a yellow oil.

Workup

  1. customTo a solution prepared
  2. customquenched by the addition of 10 mL of 1M aqueous HCl
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. washthe combined organic layers washed with brine (2×10 mL)
  5. customThe product was isolated by flash column chromatography
  6. washeluting with 0% to 10% methanol/DCM

Sources & evidence

ORD record
ord-da621218cf5c4143a300435d2e45809b
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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