Water → HCID 67402190, compound

HRID 1186422Notes

Reaction equation

HRID 1186422 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[O:4][Si:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].C(N(CC)CC)C.Cl[C:28]([O:30][CH3:31])=[O:29].O>ClCCl>[CH3:31][O:30][C:28]([N:15]1[CH2:16][CH2:17][CH:12]([CH:3]([O:4][Si:5]([CH2:8][CH3:9])([CH2:6][CH3:7])[CH2:10][CH3:11])[C:2]([F:18])([F:1])[F:19])[CH2:13][CH2:14]1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67402546HCID 67402546, compound

Product 1

HCID 67402190HCID 67402190, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[2,2,2-Trifluoro-1-(triethylsiloxy)ethyl]piperidine (303 mg, 1.02 mmol) was dissolved in dichloromethane (6 mL). To this, triethylamine (0.213 mL, 1.53 mmol) and methyl chloroformate (0.213 mL, 1.53 mmol) were added at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction was stopped by addition of water to the reaction mixture, and extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3) to give 1-methoxycarbonyl-4-[2,2,2-trifluoro-1-(triethylsiloxy)-ethyl]piperidine (287 mg, yield: 79%).

Workup

  1. dry with materialby drying over anhydrous sodium sulfate
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=17/3)

Sources & evidence

ORD record
ord-710520df70b14d819812ac43ed02307c
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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