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Iodoethane → HCID 21912745, 화합물

HRID 1245599
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HRID 1245599 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[C:16]([O:19][CH3:20])[C:15]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]([CH2:24][CH3:25])[N:17]=[C:16]([O:19][CH3:20])[C:15]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21912816HCID 21912816, 화합물

생성물 1

HCID 21912745HCID 21912745, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 30 mg (0.10 mmol) of 1-tert-butoxycarbonyl-4-(3-methoxy-4-methyl-(1H)-pyrazol-5-yl)piperidine (from Step D) in 1 mL of DMF at 0° C. was treated with 3.5 mg (0.15 mmol) of 95% NaH and 0.012 mL (0.15 mmol) of ethyliodide. After 50 minutes, the reaction was partitioned between 25 mL of EtOAc and 25 mL of brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 99:1 v/v CH2Cl2/acetone, 98:2 v/v CH2Cl2/acetone and 97:3 v/v CH2Cl2/acetone as the gradient to afford the title compound: RF: 0.39 (19:1 v/v CH2Cl2/acetone); 1H-NMR (500 MHz) δ 1.33 (t, J=7.1, 3H), 1.49 (s, 9H), 1.69–1.72 (m, 2H), 1.82–1.90 (m, 2H), 1.91 (s, 3H), 2.68–2.74 (m, 3H), 3.88 (s, 3H), 3.98 (q, J=7.1, 2H), 4.25 (m, 2H).

후처리

  1. customthe reaction was partitioned between 25 mL of EtOAc and 25 mL of brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-e6aa4454da2942a3891904f17d7a93b3
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125887B2

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