Iodine → HCID 66661021, compound

HRID 254686Notes

Reaction equation

HRID 254686 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

HCID 66661021HCID 66661021, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-ea96668e1d814ba2806cd30fefeee67b
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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