Iodine → HCID 66661021、化合物

HRID 538828ノート

反応式

HRID 538828 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 66661021HCID 66661021、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3,3-dimethylbutanal (439 mg, 4.39 mmol) in acetonitrile (8 mL) was added molecular sieves (4 Å 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)+.

後処理

  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

出典と根拠

ORDレコード
ord-942b5038064e486699ab11f563729b59
出典データセット
uspto-grants-2014_10
特許番号
US08865753B2

反応ノート

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