Hydroxylamine → HCID 86680971, compound

HRID 331527Notes

Reaction equation

HRID 331527 reaction equation
[NH2:1][OH:2].[F:3][CH2:4][CH:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1>C(O)C>[C:17]([O:16][C:15](=[O:21])[NH:14][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[N:1][OH:2])=[CH:8][CH:7]=1)[CH2:4][F:3])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86680970HCID 86680970, compound

Product 1

HCID 86680971HCID 86680971, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (459.6 μL of 50% w/v, 6.958 mmol) was added to a stirred solution of tert-butyl N-[2-fluoro-1-(4-formylphenyl)ethyl]carbamate (930 mg, 3.479 mmol) in ethanol (100 mL) and the reaction mixture stirred at ambient temperature for 4 hours. The reaction mixture was concentrated in vacuo and the residue taken up in water and extracted with ethyl acetate (×3). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give tert-butyl(2-fluoro-1-(4-((hydroxyimino)methyl)phenyl)ethyl)carbamate as an impure white solid (1058.2 mg, >100%). 1H NMR (400.0 MHz, DMSO-d6) 1.37 (s, 9H), 4.38-4.41 (m, 1H), 4.49-4.53 (m, 1H), 4.83-4.92 (m, 1H), 7.38 (d, 2H), 7.56 (d, 2H), 7.70 (d, 1H), 8.11 (d, 1H) and 11.24 (s, 1H) ppm; LC/MS m/z 227.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8aba28ec17148518b1f8f82ebaec5ef
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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