Hydroxylamine → HCID 86683834, compound

HRID 572574Notes

Reaction equation

HRID 572574 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:13]([CH3:22])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].[NH2:23][OH:24]>C(O)C>[OH:24][N:23]=[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:13]([CH3:22])[CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:10][O:11][CH3:12])=[CH:5][CH:4]=1)[NH2:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66652745HCID 66652745, compound

Product 1

HCID 86683834HCID 86683834, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-((1-(4-cyanophenyl)-2-methoxyethyl)(methyl)amino)acetate (0.136 g; 0.45 mmol) and 50% aqueous hydroxylamine (0.137 mL; 2.24 mmol) in ethanol (2 mL) was heated at 80° C. for 18 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was poured through a hydrophobic frit and evaporated in vacuo to afford the title compound (0.141 g, 93%). 1H NMR (CDCl3, 400 MHz) δ 7.78 (d, J=8.4 Hz, 2H), 7.59-7.57 (m, 2H), 6.70 (br s, 1H), 4.84 (br s, 2H), 4.05-4.02 (m, 1H), 3.71-3.67 (m, 1H), 3.63-3.60 (m, 1H), 3.40-3.35 (m, 1H), 3.34 (s, 3H), 3.21-3.16 (m, 1H), 2.40 (s, 3H), 1.49 (s, 9H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. additionThe organic phase was poured through a hydrophobic frit
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c85df10d98df4e15a42edf0127318197
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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