Pyridine → HCID 14301757, compound

HRID 868250Notes

Reaction equation

HRID 868250 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39](O)[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1CCCCC1>C(Cl)Cl.C(OCC)(=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8078CyclohexaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 14301756HCID 14301756, compound

Product 1

HCID 14301757HCID 14301757, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.85 ml of pyridine and 0.56 ml of trifluoromethanesulfonic acid anhydride were added, in that order, to a solution of 1.0 g of ethyl 6-(1-t-butoxycarbonyl-4-piperidyl)-2-hydroxyhexanoate in 10 ml of anhydrous methylene chloride, whilst cooling on an ice-salt bath, and the mixture was then stirred for 30 minuites. At the end of this time, 20 ml of a 1:1 by volume mixture of cyclohexane and ethyl acetate were added to the reaction mixture, the solution was poured onto a short column packed with silica gel, and eluted with a 1:1 volume mixture of cyclohexane and ethyl acetate. The fraction containing the title compound was concentrated by evaporation under reduced pressure, to give 0.50 g of the title compound as a syrupy substance.

Workup

  1. temperaturewhilst cooling on an ice-salt bath
  2. additionwere added to the reaction mixture
  3. additionthe solution was poured onto a short column
  4. washeluted with a 1:1 volume mixture of cyclohexane and ethyl acetate
  5. additionThe fraction containing the title compound
  6. concentrationwas concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2e9583b8cc314a1cbd65aecb19e3b87e
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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