Triethylamine → 4-Fluoro-4-(methylsulfonyloxymethyl)-1-piperidinecarboxylic acid tert-butyl ester

HRID 1095717Notes

Reaction equation

HRID 1095717 reaction equation
[F:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[F:1][C:2]1([CH2:15][O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22248400tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 222484024-Fluoro-4-(methylsulfonyloxymethyl)-1-piperidinecarboxylic acid tert-butyl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (0.150 g, 0.643 mmol) was dissolved in dichloromethane (1.8 mL) and cooled to 0° C. The solution was treated with triethylamine (0.134 ml, 0.964 mmol) followed by methanesulfonyl chloride (0.0547 ml, 0.707 mmol). The reaction was stirred at 0° C. for 2 hours then diluted with methylene chloride and quenched with saturated NH4Cl and separated. The organic layer was washed with saturated NH4Cl, 6% NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo to provide the desired product (200 mg).

Workup

  1. customquenched with saturated NH4Cl
  2. customseparated
  3. washThe organic layer was washed with saturated NH4Cl, 6% NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a647bd93549946f186b85f4de5a15933
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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