Piperidine → HCID 86718521, compound

HRID 929936Notes

Reaction equation

HRID 929936 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:19][CH3:20])[C@@H:12]([OH:18])[C:13]1[S:14][CH:15]=[CH:16][N:17]=1)C1C=CC=CC=1.N1CCCCC1.I[Si](C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.CCOC(C)=O.O>[NH2:10][C@@H:11]([CH2:19][CH3:20])[C@H:12]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[OH:18]

Participants

8

Reactant 4

HCID 8082PiperidineHCID 24477Sodium Thiosulfate2×HCID 85247Trimethylsilyl iodideHCID 131735129HCID 131735129, compound

Product 1

HCID 86718521HCID 86718521, compoundYield 134.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl((1R,2S)-1-hydroxy-1-(thiazol-2-yl)butan-2-yl)carbamate (330 mg, 1.077 mmol) in acetonitrile (25 mL) at 0° C. under argon was added piperidine (0.213 mL, 2.154 mmol) and dropwise iodotrimethylsilane (293 μL, 2.15 mmol) over a period of 5 minutes. Then, the reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 2 hours. To the reaction mixture was added at 0° C. sodium thiosulfate (500 mg), followed by water (0.5 mL), and the reaction mixture was stirred vigorously at 0° C. for 15 minutes. Further 500 mg of sodium thiosulfate was added, and the mixture was diluted with EtOAc (50 mL), dried over Na2SO4, filtered and concentrated. The residue was triturated with EtOAc, filtered, and the filtrate was concentrated to give the title compound (250 mg, 67%) as a yellow oil.

Workup

  1. stirringthe reaction mixture was stirred vigorously at 0° C. for 15 minutes
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with EtOAc
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-280ba9c1b87f49048a91fe5d21d665a6
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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