Potassium Carbonate → HCID 86708541, compound

HRID 1430852Notes

Reaction equation

HRID 1430852 reaction equation
[OH:1][CH2:2][C@H:3]1[N:8]([CH2:9][C:10]([CH3:12])=[CH2:11])[CH2:7][CH2:6][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4]1.[I:20]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[I:20][CH2:11][C:10]1([CH3:12])[O:1][CH2:2][C@@H:3]2[CH2:4][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:7][N:8]2[CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120273N-IodosuccinimideHCID 86708542HCID 86708542, compound

Product 1

HCID 86708541HCID 86708541, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask charged with (S)-tert-butyl 3-(hydroxymethyl)-4-(2-methylallyl)piperazine-1-carboxylate (0.1 g, 0.370 mmol) in acetonitrile (3.70 ml) was added N-iodosuccinimide (0.125 g, 0.555 mmol) and potassium carbonate (0.077 g, 0.555 mmol). The reaction mixture was stirred at rt ON. The reaction mixture was quenched with 20% sodium thiosulfate solution and stirred 30 min. The mixture was transferred to a separatory funnel and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. (9aS)-tert-butyl 3-(iodomethyl)-3-methylhexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (0.156 g) was isolated as a yellow oil. Material used crude in subsequent chemistry.

Workup

  1. customThe reaction mixture was quenched with 20% sodium thiosulfate solution
  2. stirringstirred 30 min
  3. customThe mixture was transferred to a separatory funnel
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c418c589924241e0bdfef515b11dd7e7
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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