1,5-Diphenylpentan-3-one → N-(1,5-Diphenylpent-3-yl)hydroxylamine

HRID 1078102

反応式

HRID 1078102 の反応式
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CC(O)C>[C:1]1([CH2:7][CH2:8][CH:9]([NH:20][OH:21])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 214961,5-Diphenylpentan-3-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 22910035N-(1,5-Diphenylpent-3-yl)hydroxylamine収率 30.6%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 0.37 g (1.55 mmol) of 1,5-diphenyl-3-pentanone in 20 ml of 2-propanol was treated with 0.22 g (3.1 mmol) of hydroxylamine hydrochloride and 0.31 g (4.7 mmol) of anhydrous sodium acetate. After being stirred for 10 min, the mixture was treated with 0.20 g (3.2 mmol) of sodium cyanoborohydride and stirred at ambient temperature for 16 h. After concentration in vacuo, the residue was taken up in ethyl acetate, washed sequentially with aqueous NaHCO3 and saturated brine, dried over MgSO4, and concentrated. Flash chromatography using 40% ethyl acetate in chloroform gave 121 mg (31%) of the desired compound (Rf 0.16, 30% ethyl acetate in chloroform) as a white solid, m.p. 54°-55° C. 1H NMR (CDCl3) δ1.7-1.85 (m, 2H), 1.85-2.0 (m, 2H), 2.6-2.75 (m, 4H), 2.90 (pentet, J=6 Hz, 1H), 5.22 (br, 2H), 7.1-7.35 (m, 10H). Mass spectrum (M+H)+ =256.

後処理

  1. stirringstirred at ambient temperature for 16 h
  2. concentrationAfter concentration in vacuo
  3. washwashed sequentially with aqueous NaHCO3 and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6cc1a4385b99425cb52c8c7e210cb436
出典データセット
uspto-grants-1996_08
特許番号
US05545750

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