Acetonitrile → 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanamine

HRID 1509316ノート

反応式

HRID 1509316 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(N)=O)[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.C1([I+2])C=CC=CC=1.[Na].C(#[N:43])C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:43])[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 5360545SodiumHCID 672542661-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarboxamideHCID 178525681HCID 178525681、化合物

生成物 1

HCID 672570841-(4-Bromophenyl)-3,3-dimethoxycyclobutanamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarboxamide (2.3 g, 7.32 mmol) in acetonitrile (9 ml) and Water (9.00 ml) was added phenyliodine bis(trifluoroacetate) (4.73 g, 11.00 mmol) and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was slowly poured into sodium bicarnate sat. solution (˜45 ml) and extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with water, brine and concentrated to give crude product (3.4 g). The crude product was purified by column (biotage, 50 g) eluted with 0-5% DCM/Methanol (mixture of 500 ml methanol and 60 ml 2M NH4OH in methanol) to give product 1-(4-bromophenyl)-3,3-dimethoxycyclobutanamine (1.06 g), 1H NMR (500 MHz, CDCl3): 7.48 (d, 2H), 7.32 (d, 2H), 3.27 (d, 3H), 3.17 (d, 3H), 2.66 (d, 2H), 2.44 (d, 2H).

後処理

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe combined organic phase was washed with water, brine
  3. concentrationconcentrated
  4. customto give crude product (3.4 g)
  5. customThe crude product was purified by column (biotage, 50 g)
  6. washeluted with 0-5% DCM/Methanol (mixture of 500 ml methanol and 60 ml 2M NH4OH in methanol)

出典と根拠

ORDレコード
ord-0080b0cb144e45159da1b468f2549838
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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