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

HRID 704486ノート

反応式

HRID 704486 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21889567Chloroform ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5f0eedc7ac5547d2b7e1c4d04400cc41
出典データセット
uspto-grants-1991_01
特許番号
US04987253

反応ノート

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