Trifluoromethanesulfonic anhydride → HCID 53725706, compound

HRID 380531Notes

Reaction equation

HRID 380531 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([CH3:29])([CH3:28])C)N=1)(C)(C)C.FC(F)(F)[S:32](OS(C(F)(F)F)(=O)=O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][S:32][CH2:29][C:26]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridineHCID 516892Sodium BicarbonateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 53725706HCID 53725706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 500 mg (2.32 mmol) of 1-t-butoxycarbonyl-4-(hydroxymethyl)piperidine (Example 201) and 1 mL (4.5 mmol) of 2,6-di-t-butylpyridine in 10 mL of CH2Cl2 was added 0.4 mL (2.32 mmol) of triflouromethanesulfonic anhydride at −78° C. After stirring for 0.5 h, 0.5 mL (4.5 mmol) of benzylmercaptane were added. The mixture was warmed to 0° C. and allowed to stir for another 15 min. 10 mL of sat'd NaHCO3 solution were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1) to give the title compound.

Workup

  1. addition0.5 mL (4.5 mmol) of benzylmercaptane were added
  2. stirringto stir for another 15 min
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic fractions were washed with sat'd NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-d7cd8056cc0b4d31b35c06c7bfcefc61
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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