Iodine → HCID 66661021, 화합물

HRID 254686노트

반응식

HRID 254686 반응식
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[NH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[S-:23][C:24]#[N:25].[K+].II.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[C:2]([C:3]1[S:23][C:24](=[NH:25])[N:8]([CH2:9][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=1)([CH3:7])([CH3:6])[CH3:1]

참가 물질

7

반응물 5

HCID 807IodineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 656671Sodium PyrosulfiteHCID 1502021tert-Butyl (2R)-2-(aminomethyl)piperidine-1-carboxylate

생성물 1

HCID 66661021HCID 66661021, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 3,3-dimethylbutanal (439 mg, 4.39 mmol) in acetonitrile (8 mL) was added molecular sieves (4A beads, 8-12 mesh, 0.7 g) and (R)-tert-butyl 2-(aminomethyl)piperidine-1-carboxylate (940 mg, 4.39 mmol). The mixture was stirred for 12 hr at room temperature, filtered and washed with acetonitrile (5 mL). To this solution was added potassium thiocyanate (567 mg, 5.83 mmol) and the temperature was adjusted at 50° C. The reaction was stirred until all solids were dissolved then iodine (1.13 g, 4.39 mmol) was added. The reaction was stirred at 50° C. for 12 hr. The mixture was then stirred with 20% sodium metabisulfite for 1 hr. Then the organic layer was separated and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. This intermediate was used without further purification. MS (DCI/NH3) m/z 354 (M+H)+.

후처리

  1. filtrationfiltered
  2. washwashed with acetonitrile (5 mL)
  3. customwas adjusted at 50° C
  4. stirringThe reaction was stirred until all solids
  5. dissolutionwere dissolved
  6. stirringThe reaction was stirred at 50° C. for 12 hr
  7. customThen the organic layer was separated
  8. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
  9. dry with materialThe combined organics were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ea96668e1d814ba2806cd30fefeee67b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875640B2

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