Hydroxyamine hydrochloride → HCID 86714669, compound

HRID 1409459Notes

Reaction equation

HRID 1409459 reaction equation
[Si:1]([O:18][CH:19]([CH3:22])[C:20]#[N:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][OH:24].Cl.C([O-])(O)=O.[Na+]>CO>[Si:1]([O:18][CH:19]([CH3:22])[C:20](=[N:23][OH:24])[NH2:21])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 70981387HCID 70981387, compound

Product 1

HCID 86714669HCID 86714669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Into a flask containing 2-((tert-butyldiphenylsilyl)oxy)propanenitrile (14.6 mmol, 4.5 g) in MeOH (50 ml), NH2OH.HCl (29.1 mmol, 2 g) and NaHCO3 (43.7 mmol, 3.6 g) were added. The resulting mixture was stirred at 70° C. for overnight. The mixture was quenched with H2O and extracted with EtOAc. The organic layer was washed with H2O, dried, filtered and evaporated. Yield 4.02 g. 1H-NMR (400 MHz; DMSO-d6): δ 1.01 (s, 9H), 1.20 (d, 3H), 4.12 (q, 1H), 7.38-7.46 (m, 6H), 7.60-7.64 (m, 4H). LC-MS: [M+1]=343.12.

Workup

  1. additionwere added
  2. customThe mixture was quenched with H2O
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a5a8f84eb71e44c9add8db59f1cca64d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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