Trifluoroacetic acid → O-Benzyl-N-(4-cyanobutyl)hydroxylamine

HRID 704486Notes

Reaction equation

HRID 704486 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]S([O-])(=O)=O.[Ca+2]>CCO.C(Cl)(Cl)Cl>[CH2:8]([O:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24497Calcium SulfateHCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamate

Product 1

HCID 14078488O-Benzyl-N-(4-cyanobutyl)hydroxylamineYield 75.4%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

Trifluoroacetic acid (TFA, 16 mL) was added to (B) (2.59 g, 8.51 mmol), and the solution stirred at room temperature for 20 min (Drierite tube). Excess TFA was removed on the rotovap, saturated NaHCO3 (50 mL) was added and the product was extracted into ether (3×50 mL). After a brine wash (50 mL), the organic extracts were concentrated to yield 1.77 g crude product. Column chromatography with 3% EtOH/CHCl3 furnished 1.31 g of (3) (75% yield), which has been previously prepared: NMR δ1.5-1.7 (m, 4 H), 2.16-2.35 (m, 2 H), 2.78-2.98 (m, 2 H), 4.66 (s, 2 H), 5.45 (br s, 1 H), 7.28 (s, 5 H).

Workup

  1. customExcess TFA was removed on the rotovap, saturated NaHCO3 (50 mL)
  2. additionwas added
  3. extractionthe product was extracted into ether (3×50 mL)
  4. washAfter a brine wash (50 mL)
  5. concentrationthe organic extracts were concentrated
  6. customto yield 1.77 g crude product

Sources & evidence

ORD record
ord-5f0eedc7ac5547d2b7e1c4d04400cc41
Source dataset
uspto-grants-1991_01
Patent number
US04987253

Reaction notes

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