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

HRID 1509316노트

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HRID 1509316 반응식
[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

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 5360545SodiumHCID 672542661-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarboxamideHCID 178525681HCID 178525681, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0080b0cb144e45159da1b468f2549838
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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