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

HRID 704486

반응식

HRID 704486 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21889567Chloroform ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5f0eedc7ac5547d2b7e1c4d04400cc41
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04987253

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